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Search for "three component synthesis" in Full Text gives 34 result(s) in Beilstein Journal of Organic Chemistry.
Lewis acid-promoted direct synthesis of isoxazole derivatives
- Dengxu Qiu,
- Chenhui Jiang,
- Pan Gao and
- Yu Yuan
Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113
- reported [16]. In 2015, Yang’s group [10][17] reported the copper-catalyzed conversion of methylarenes into isoxazole derivatives with KNO3 as the source of nitrile oxide (Scheme 1, reaction 1). In 2019, Deng’s group [18] developed a three-component synthesis method of isoxazole derivatives using TBN as
Graphical Abstract
Figure 1: Natural products and drug molecules containing isoxazole moieties.
Scheme 1: Traditional methods for the synthesis of isoxazoles and the current approach.
Scheme 2: Reaction scope of alkynes. Conditions: 1 (0.1 mmol, 1 equiv), 2a (0.2 mmol, 2 equiv), AlCl3 (0.3 mm...
Figure 2: Crystal structure of 3i.
Scheme 3: Reaction substrate scope of quinolines. Conditions: 1a (0.1 mmol, 1 equiv), 2 (0.2 mmol, 2 equiv), ...
Scheme 4: Gram scale reaction.
Scheme 5: Control experiments and possible reaction mechanism.
Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence
- Nadia Ledermann,
- Alae-Eddine Moubsit and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99
- summary the indole anion intermediate resulting from a one-pot alkynylation–cyclization sequence, which has been previously shown to be efficiently trapped by carbon electrophiles to give N-substituted indoles in a consecutive three-component synthesis, can be selectively iodinated in the 3-position with
- three-component synthesis and conception of a consecutive alkynylation–cyclization–iodination–alkylation four-component synthesis via an (aza)indole anion intermediate. Consecutive alkynylation–cyclization–iodination–alkylation four-component synthesis of trisubstituted 3-iodoindoles (awith 2,4
Graphical Abstract
Scheme 1: Consecutive alkynylation–cyclization–alkylation three-component synthesis and conception of a conse...
Scheme 2: Consecutive alkynylation–cyclization–iodination–alkylation four-component synthesis of trisubstitut...
Scheme 3: Consecutive double alkynylation–cyclization–iodination–alkylation pseudo-five-component synthesis o...
Scheme 4: Suzuki coupling of 3-iodoindole 5a with arylboronic acids 7 to give 1,2,3-trisubstituted indoles 8.
Figure 1: A: Absorption and emission spectra of 1-methyl-2-phenyl-3-(p-tolyl)-1H-indole (8b), recorded in dic...
Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates
- Bastian Jakob,
- Nico Schneider,
- Luca Gengenbach and
- Georg Manolikakes
Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52
Graphical Abstract
Figure 1: Biologically active molecules containing α-arylglycine motifs (highlighted in green and blue).
Scheme 1: The Petasis reaction – fundamental reactivities and recent developments.
Scheme 2: Observations from previous studies and mechanistic rationale.
Scheme 3: Initial experiments.
Scheme 4: Reaction scope – aryltrifluoroborates (yields and enantiomeric ratios in parentheses refer to our p...
Scheme 5: Synthesis of both enantiomers of arylglycine building block 18.
Microwave-assisted efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines
- Moustafa Sherief Moustafa,
- Ramadan Ahmed Mekheimer,
- Saleh Mohammed Al-Mousawi,
- Mohamed Abd-Elmonem,
- Hesham El-Zorba,
- Afaf Mohamed Abdel Hameed,
- Tahany Mahmoud Mohamed and
- Kamal Usef Sadek
Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142
- formation of products 4. Microwave three-component synthesis of triazines 4a–j. Selected bond lengths and bond angles for compound 4i. Supporting Information Supporting Information File 122: NMR and mass spectra. Funding K. U. Sadek is grateful to the Alexander von Humboldt Foundation for donation of a
Graphical Abstract
Scheme 1: Previously reported methods for the synthesis of 1,3,5-triazine-2,4-diamine derivatives.
Scheme 2: One-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines 4a...
Figure 1: ORTEP diagram of compound 4i.
Scheme 3: Plausible different routes to account for the formation of products 4.
A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions
- Pezhman Shiri and
- Jasem Aboonajmi
Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52
Graphical Abstract
Scheme 1: Chemical structure of the catalysts 1a and 1b and their catalytic application in CuAAC reactions.
Scheme 2: Synthetic route to the catalyst 11 and its catalytic application in CuAAC reactions.
Scheme 3: Synthetic route of dendrons, illustrated using G2-AMP 23.
Scheme 4: The catalytic application of CuYAu–Gx-AAA–SBA-15 in a CuAAC reaction.
Scheme 5: Synthetic route to the catalyst 36.
Scheme 6: Application of the catalyst 36 in CuAAC reactions.
Scheme 7: The synthetic route to the catalyst 45 and catalytic application of 45 in “click” reactions.
Scheme 8: Synthetic route to the catalyst 48 and catalytic application of 48 in “click” reactions.
Scheme 9: Synthetic route to the catalyst 58 and catalytic application of 58 in “click” reactions.
Scheme 10: Synthetic route to the catalyst 64 and catalytic application of 64 in “click” reactions.
Scheme 11: Chemical structure of the catalyst 68 and catalytic application of 68 in “click” reactions.
Scheme 12: Chemical structure of the catalyst 69 and catalytic application of 69 in “click” reactions.
Scheme 13: Synthetic route to, and chemical structure of the catalyst 74.
Scheme 14: Application of the cayalyst 74 in “click” reactions.
Scheme 15: Synthetic route to, and chemical structure of the catalyst 78 and catalytic application of 78 in “c...
Scheme 16: Synthetic route to the catalyst 85.
Scheme 17: Application of the catalyst 85 in “click” reactions.
Scheme 18: Synthetic route to the catalyst 87 and catalytic application of 87 in “click” reactions.
Scheme 19: Chemical structure of the catalyst 88 and catalytic application of 88 in “click” reactions.
Scheme 20: Synthetic route to the catalyst 90 and catalytic application of 90 in “click” reactions.
Scheme 21: Synthetic route to the catalyst 96 and catalytic application of 96 in “click” reactions.
Scheme 22: Synthetic route to the catalyst 100 and catalytic application of 100 in “click” reactions.
Scheme 23: Synthetic route to the catalyst 102 and catalytic application of 23 in “click” reactions.
Scheme 24: Synthetic route to the catalysts 108–111.
Scheme 25: Catalytic application of 108–111 in “click” reactions.
Scheme 26: Synthetic route to the catalyst 121 and catalytic application of 121 in “click” reactions.
Scheme 27: Synthetic route to 125 and application of 125 in “click” reactions.
Scheme 28: Synthetic route to the catalyst 131 and catalytic application of 131 in “click” reactions.
Scheme 29: Synthetic route to the catalyst 136.
Scheme 30: Application of the catalyst 136 in “click” reactions.
Scheme 31: Synthetic route to the catalyst 141 and catalytic application of 141 in “click” reactions.
Scheme 32: Synthetic route to the catalyst 144 and catalytic application of 144 in “click” reactions.
Scheme 33: Synthetic route to the catalyst 149 and catalytic application of 149 in “click” reactions.
Scheme 34: Synthetic route to the catalyst 153 and catalytic application of 153 in “click” reactions.
Scheme 35: Synthetic route to the catalyst 155 and catalytic application of 155 in “click” reactions.
Scheme 36: Synthetic route to the catalyst 157 and catalytic application of 157 in “click” reactions.
Scheme 37: Synthetic route to the catalyst 162.
Scheme 38: Application of the catalyst 162 in “click” reactions.
Scheme 39: Synthetic route to the catalyst 167 and catalytic application of 167 in “click” reactions.
Scheme 40: Synthetic route to the catalyst 169 and catalytic application of 169 in “click” reactions.
Scheme 41: Synthetic route to the catalyst 172.
Scheme 42: Application of the catalyst 172 in “click” reactions.
In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
- Irina G. Tkachenko,
- Sergey A. Komykhov,
- Vladimir I. Musatov,
- Svitlana V. Shishkina,
- Viktoriya V. Dyakonenko,
- Vladimir N. Shvets,
- Mikhail V. Diachkov,
- Valentyn A. Chebanov and
- Sergey M. Desenko
Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231
- catalyst. Another example of a 1,3-dicarbonyl compound that often exhibits unusual behavior in the three-component synthesis of azolopyrimidines [27][29] is ethyl 4,4,4-trifluoroacetoacetate (13). In these transformations, the last reaction step, a water elimination, sometimes does not occur, and the final
Graphical Abstract
Scheme 1: Three synthetic approaches to dihydrotetrazolo[1,5-a]pyrimidines.
Scheme 2: Three-component reaction of 1, 7a,b and 8a–d in water.
Figure 1: Molecular structure of 9a according to X-ray data. Displacement ellipsoids are shown at the 50% pro...
Scheme 3: Three-component reaction of 5-aminotetrazole (1) with formaldehyde (7a) and acetylacetone (10).
Scheme 4: a) Three-component reaction of 5-aminotetrazole (1) with acetaldehyde (7b) and ethyl 4,4,4-trifluor...
Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage
- Gagandeep Kour Reen,
- Ashok Kumar and
- Pratibha Sharma
Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165
Graphical Abstract
Figure 1: Various drugs having IP nucleus.
Figure 2: Participation percentage of various TMs for the syntheses of IPs.
Scheme 1: CuI–NaHSO4·SiO2-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 2: Experimental examination of reaction conditions.
Scheme 3: One-pot tandem reaction for the synthesis of 2-haloimidazopyridines.
Scheme 4: Mechanistic scheme for the synthesis of 2-haloimidazopyridine.
Scheme 5: Copper-MOF-catalyzed three-component reaction (3-CR) for imidazo[1,2-a]pyridines.
Scheme 6: Mechanism for copper-MOF-driven synthesis.
Scheme 7: Heterogeneous synthesis via titania-supported CuCl2.
Scheme 8: Mechanism involving oxidative C–H functionalization.
Scheme 9: Heterogeneous synthesis of IPs.
Scheme 10: One-pot regiospecific synthesis of imidazo[1,2-a]pyridines.
Scheme 11: Vinyl azide as an unprecedented substrate for imidazo[1,2-a]pyridines.
Scheme 12: Radical pathway.
Scheme 13: Cu(I)-catalyzed transannulation approach for imidazo[1,5-a]pyridines.
Scheme 14: Plausible radical pathway for the synthesis of imidazo[1,5-a]pyridines.
Scheme 15: A solvent-free domino reaction for imidazo[1,2-a]pyridines.
Scheme 16: Cu-NPs-mediated synthesis of imidazo[1,2-a]pyridines.
Scheme 17: CuI-catalyzed synthesis of isoxazolylimidazo[1,2-a]pyridines.
Scheme 18: Functionalization of 4-bromo derivative via Sonogashira coupling reaction.
Scheme 19: A plausible reaction pathway.
Scheme 20: Cu(I)-catalyzed intramolecular oxidative C–H amidation reaction.
Scheme 21: One-pot synthetic reaction for imidazo[1,2-a]pyridine.
Scheme 22: Plausible reaction mechanism.
Scheme 23: Cu(OAc)2-promoted synthesis of imidazo[1,2-a]pyridines.
Scheme 24: Mechanism for aminomethylation/cycloisomerization of propiolates with imines.
Scheme 25: Three-component synthesis of imidazo[1,2-a]pyridines.
Figure 3: Scope of pyridin-2(1H)-ones and acetophenones.
Scheme 26: CuO NPS-promoted A3 coupling reaction.
Scheme 27: Cu(II)-catalyzed C–N bond formation reaction.
Scheme 28: Mechanism involving Chan–Lam/Ullmann coupling.
Scheme 29: Synthesis of formyl-substituted imidazo[1,2-a]pyridines.
Scheme 30: A tandem sp3 C–H amination reaction.
Scheme 31: Probable mechanistic approach.
Scheme 32: Dual catalytic system for imidazo[1,2-a]pyridines.
Scheme 33: Tentative mechanism.
Scheme 34: CuO/CuAl2O4/ᴅ-glucose-promoted 3-CCR.
Scheme 35: A tandem CuOx/OMS-2-based synthetic strategy.
Figure 4: Biomimetic catalytic oxidation in the presence of electron-transfer mediators (ETMs).
Scheme 36: Control experiment.
Scheme 37: Copper-catalyzed C(sp3)–H aminatin reaction.
Scheme 38: Reaction of secondary amines.
Scheme 39: Probable mechanistic pathway.
Scheme 40: Coupling reaction of α-azidoketones.
Scheme 41: Probable pathway.
Scheme 42: Probable mechanism with free energy calculations.
Scheme 43: MCR for cyanated IP synthesis.
Scheme 44: Substrate scope for the reaction.
Scheme 45: Reaction mechanism.
Scheme 46: Probable mechanistic pathway for Cu/ZnAl2O4-catalyzed reaction.
Scheme 47: Copper-catalyzed double oxidative C–H amination reaction.
Scheme 48: Application towards different coupling reactions.
Scheme 49: Reaction mechanism.
Scheme 50: Condensation–cyclization approach for the synthesis of 1,3-diarylated imidazo[1,5-a]pyridines.
Scheme 51: Optimized reaction conditions.
Scheme 52: One-pot 2-CR.
Scheme 53: One-pot 3-CR without the isolation of chalcone.
Scheme 54: Copper–Pybox-catalyzed cyclization reaction.
Scheme 55: Mechanistic pathway catalyzed by Cu–Pybox complex.
Scheme 56: Cu(II)-promoted C(sp3)-H amination reaction.
Scheme 57: Wider substrate applicability for the reaction.
Scheme 58: Plausible reaction mechanism.
Scheme 59: CuI assisted C–N cross-coupling reaction.
Scheme 60: Probable reaction mechanism involving sp3 C–H amination.
Scheme 61: One-pot MCR-catalyzed by CoFe2O4/CNT-Cu.
Scheme 62: Mechanistic pathway.
Scheme 63: Synthetic scheme for 3-nitroimidazo[1,2-a]pyridines.
Scheme 64: Plausible mechanism for CuBr-catalyzed reaction.
Scheme 65: Regioselective synthesis of halo-substituted imidazo[1,2-a]pyridines.
Scheme 66: Synthesis of 2-phenylimidazo[1,2-a]pyridines.
Scheme 67: Synthesis of diarylated compounds.
Scheme 68: CuBr2-mediated one-pot two-component oxidative coupling reaction.
Scheme 69: Decarboxylative cyclization route to synthesize 1,3-diarylimidazo[1,5-a]pyridines.
Scheme 70: Mechanistic pathway.
Scheme 71: C–H functionalization reaction of enamines to produce diversified heterocycles.
Scheme 72: A plausible mechanism.
Scheme 73: CuI-promoted aerobic oxidative cyclization reaction of ketoxime acetates and pyridines.
Scheme 74: CuI-catalyzed pathway for the formation of imidazo[1,2-a]pyridine.
Scheme 75: Mechanistic pathway.
Scheme 76: Mechanistic rationale for the synthesis of products.
Scheme 77: Copper-catalyzed synthesis of vinyloxy-IP.
Scheme 78: Regioselective product formation with propiolates.
Scheme 79: Proposed mechanism for vinyloxy-IP formation.
Scheme 80: Regioselective synthesis of 3-hetero-substituted imidazo[1,2-a]pyridines with different reaction su...
Scheme 81: Mechanistic pathway.
Scheme 82: CuI-mediated synthesis of 3-formylimidazo[1,2-a]pyridines.
Scheme 83: Radical pathway for 3-formylated IP synthesis.
Scheme 84: Pd-catalyzed urea-cyclization reaction for IPs.
Scheme 85: Pd-catalyzed one-pot-tandem amination and intramolecular amidation reaction.
Figure 5: Scope of aniline nucleophiles.
Scheme 86: Pd–Cu-catalyzed Sonogashira coupling reaction.
Scheme 87: One-pot amide coupling reaction for the synthesis of imidazo[4,5-b]pyridines.
Scheme 88: Urea cyclization reaction for the synthesis of two series of pyridines.
Scheme 89: Amidation reaction for the synthesis of imidazo[4,5-b]pyridines.
Figure 6: Amide scope.
Scheme 90: Pd NPs-catalyzed 3-component reaction for the synthesis of 2,3-diarylated IPs.
Scheme 91: Plausible mechanistic pathway for Pd NPs-catalyzed MCR.
Scheme 92: Synthesis of chromenoannulated imidazo[1,2-a]pyridines.
Scheme 93: Mechanism for the synthesis of chromeno-annulated IPs.
Scheme 94: Zinc oxide NRs-catalyzed synthesis of imidazo[1,2-a]azines/diazines.
Scheme 95: Zinc oxide-catalyzed isocyanide based GBB reaction.
Scheme 96: Reaction pathway for ZnO-catalyzed GBB reaction.
Scheme 97: Mechanistic pathway.
Scheme 98: ZnO NRs-catalyzed MCR for the synthesis of imidazo[1,2-a]azines.
Scheme 99: Ugi type GBB three-component reaction.
Scheme 100: Magnetic NPs-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 101: Regioselective synthesis of 2-alkoxyimidazo[1,2-a]pyridines catalyzed by Fe-SBA-15.
Scheme 102: Plausible mechanistic pathway for the synthesis of 2-alkoxyimidazopyridine.
Scheme 103: Iron-catalyzed synthetic approach.
Scheme 104: Iron-catalyzed aminooxygenation reaction.
Scheme 105: Mechanistic pathway.
Scheme 106: Rh(III)-catalyzed double C–H activation of 2-substituted imidazoles and alkynes.
Scheme 107: Plausible reaction mechanism.
Scheme 108: Rh(III)-catalyzed non-aromatic C(sp2)–H bond activation–functionalization for the synthesis of imid...
Scheme 109: Reactivity and selectivity of different substrates.
Scheme 110: Rh-catalyzed direct C–H alkynylation by Li et al.
Scheme 111: Suggested radical mechanism.
Scheme 112: Scandium(III)triflate-catalyzed one-pot reaction and its mechanism for the synthesis of benzimidazo...
Scheme 113: RuCl3-assisted Ugi-type Groebke–Blackburn condensation reaction.
Scheme 114: C-3 aroylation via Ru-catalyzed two-component reaction.
Scheme 115: Regioselective synthetic mechanism.
Scheme 116: La(III)-catalyzed one-pot GBB reaction.
Scheme 117: Mechanistic approach for the synthesis of imidazo[1,2-a]pyridines.
Scheme 118: Synthesis of imidazo[1,2-a]pyridine using LaMnO3 NPs under neat conditions.
Scheme 119: Mechanistic approach.
Scheme 120: One-pot 3-CR for regioselective synthesis of 2-alkoxy-3-arylimidazo[1,2-a]pyridines.
Scheme 121: Formation of two possible products under optimization of the catalysts.
Scheme 122: Mechanistic strategy for NiFe2O4-catalyzed reaction.
Scheme 123: Two-component reaction for synthesizing imidazodipyridiniums.
Scheme 124: Mechanistic scheme for the synthesis of imidazodipyridiniums.
Scheme 125: CuI-catalyzed arylation of imidazo[1,2-a]pyridines.
Scheme 126: Mechanism for arylation reaction.
Scheme 127: Cupric acetate-catalyzed double carbonylation approach.
Scheme 128: Radical mechanism for double carbonylation of IP.
Scheme 129: C–S bond formation reaction catalyzed by cupric acetate.
Scheme 130: Cupric acetate-catalyzed C-3 formylation approach.
Scheme 131: Control experiments for signifying the role of DMSO and oxygen.
Scheme 132: Mechanism pathway.
Scheme 133: Copper bromide-catalyzed CDC reaction.
Scheme 134: Extension of the substrate scope.
Scheme 135: Plausible radical pathway.
Scheme 136: Transannulation reaction for the synthesis of imidazo[1,5-a]pyridines.
Scheme 137: Plausible reaction pathway for denitrogenative transannulation.
Scheme 138: Cupric acetate-catalyzed C-3 carbonylation reaction.
Scheme 139: Plausible mechanism for regioselective C-3 carbonylation.
Scheme 140: Alkynylation reaction at C-2 of 3H-imidazo[4,5-b]pyridines.
Scheme 141: Two-way mechanism for C-2 alkynylation of 3H-imidazo[4,5-b]pyridines.
Scheme 142: Palladium-catalyzed SCCR approach.
Scheme 143: Palladium-catalyzed Suzuki coupling reaction.
Scheme 144: Reaction mechanism.
Scheme 145: A phosphine free palladium-catalyzed synthesis of C-3 arylated imidazopyridines.
Scheme 146: Palladium-mediated Buchwald–Hartwig cross-coupling reaction.
Figure 7: Structure of the ligands optimized.
Scheme 147: Palladium acetate-catalyzed direct arylation of imidazo[1,2-a]pyridines.
Scheme 148: Palladium acetate-catalyzed mechanistic pathway.
Scheme 149: Palladium acetate-catalyzed regioselective arylation reported by Liu and Zhan.
Scheme 150: Mechanism for selective C-3 arylation of IP.
Scheme 151: Pd(II)-catalyzed alkenylation reaction with styrenes.
Scheme 152: Pd(II)-catalyzed alkenylation reaction with acrylates.
Scheme 153: A two way mechanism.
Scheme 154: Double C–H activation reaction catalyzed by Pd(OAc)2.
Scheme 155: Probable mechanism.
Scheme 156: Palladium-catalyzed decarboxylative coupling.
Scheme 157: Mechanistic cycle for decarboxylative arylation reaction.
Scheme 158: Ligand-free approach for arylation of imidazo[1,2-a]pyridine-3-carboxylic acids.
Scheme 159: Mechanism for ligandless arylation reaction.
Scheme 160: NHC-Pd(II) complex assisted arylation reaction.
Scheme 161: C-3 arylation of imidazo[1,2-a]pyridines with aryl bromides catalyzed by Pd(OAc)2.
Scheme 162: Pd(II)-catalyzed C-3 arylations with aryl tosylates and mesylates.
Scheme 163: CDC reaction for the synthesis of imidazo[1,2-a]pyridines.
Scheme 164: Plausible reaction mechanism for Pd(OAc)2-catalyzed synthesis of imidazo[1,2-a]pyridines.
Scheme 165: Pd-catalyzed C–H amination reaction.
Scheme 166: Mechanism for C–H amination reaction.
Scheme 167: One-pot synthesis for 3,6-di- or 2,3,6-tri(hetero)arylimidazo[1,2-a]pyridines.
Scheme 168: C–H/C–H cross-coupling reaction of IPs and azoles catalyzed by Pd(II).
Scheme 169: Mechanistic cycle.
Scheme 170: Rh-catalyzed C–H arylation reaction.
Scheme 171: Mechanistic pathway for C–H arylation of imidazo[1,2-a]pyridine.
Scheme 172: Rh(III)-catalyzed double C–H activation of 2-phenylimidazo[1,2-a]pyridines and alkynes.
Scheme 173: Rh(III)-catalyzed mechanistic pathway.
Scheme 174: Rh(III)-mediated oxidative coupling reaction.
Scheme 175: Reactions showing functionalization of the product obtained by the group of Kotla.
Scheme 176: Mechanism for Rh(III)-catalyzed oxidative coupling reaction.
Scheme 177: Rh(III)-catalyzed C–H activation reaction.
Scheme 178: Mechanistic cycle.
Scheme 179: Annulation reactions of 2-arylimidazo[1,2-a]pyridines and alkynes.
Scheme 180: Two-way reaction mechanism for annulations reaction.
Scheme 181: [RuCl2(p-cymene)]2-catalyzed C–C bond formation reaction.
Scheme 182: Reported reaction mechanism.
Scheme 183: Fe(III) catalyzed C-3 formylation approach.
Scheme 184: SET mechanism-catalyzed by Fe(III).
Scheme 185: Ni(dpp)Cl2-catalyzed KTC coupling.
Scheme 186: Pd-catalyzed SM coupling.
Scheme 187: Vanadium-catalyzed coupling of IP and NMO.
Scheme 188: Mechanistic cycle.
Scheme 189: Selective C3/C5–H bond functionalizations by mono and bimetallic systems.
Scheme 190: rGO-Ni@Pd-catalyzed C–H bond arylation of imidazo[1,2-a]pyridine.
Scheme 191: Mechanistic pathway for heterogeneously catalyzed arylation reaction.
Scheme 192: Zinc triflate-catalyzed coupling reaction of substituted propargyl alcohols.
One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion
- Christina Görgen,
- Katharina Boden,
- Guido J. Reiss,
- Walter Frank and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136
- consecutive three-component process clearly is superior. With four bond-forming steps (activation, alkynylation, Michael addition, and cyclization) the average yield per bond-forming step accounts to 94%. With the optimized conditions of the consecutive three-component synthesis in hand (hetero)arylglyoxylic
- analyses. Additionally, the structure was corroborated by an X-ray structure analysis of compound 5r showing dimers held together by inter- and intramolecular hydrogen bonding (Figure 5) [53]. The three-component synthesis allows addressing three points of diversity and especially for the hydrazide
- cyclizing processes, eventually in a one-pot fashion. Further studies exploring the dense electrophilic reactivity of ynediones in consecutive multicomponent reactions are still underway. Experimental Typical procedure for the three-component synthesis of compound 5b: In an oven-dried Schlenk flask equipped
Graphical Abstract
Figure 1: Selected anticancer active 3,5-diaryl-1-acylpyrazoline (left) and xanthine oxygenase inhibitors (ce...
Figure 2: Selected 1-acyl-5-hydroxypyrazolines with analgesic (left, center) and antibacterial activity (cent...
Scheme 1: Glyoxylation–alkynylation (GA) and activation–alkynylation (AA) synthesis of alkynediones in a one-...
Scheme 2: Consecutive three-component synthesis to give 5-benzoyl-3-phenyl-1H-pyrazole (6a) after alkaline de...
Figure 3: ORTEP plot of 5-benzoyl-3-phenyl-1H-pyrazole (6a) (thermal ellipsoids at 30% probability); the dire...
Scheme 3: Cyclization of 1,4-diphenylbut-3-yne-1,2-dione (3a) and Boc-hydrazine (4a) to give intermediate 5a.
Figure 4: Ellipsoid plot of 1-Boc-5-benzoyl-5-hydroxypyrazoline 5a.
Scheme 4: Model reaction for optimizing the activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hyd...
Scheme 5: One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines 5.
Figure 5: ORTEP plot and dimer of compound 5r (thermal ellipsoids at 30% probability).
Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams
- Edorta Martínez de Marigorta,
- Jesús M. de Los Santos,
- Ana M. Ochoa de Retana,
- Javier Vicario and
- Francisco Palacios
Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104
- formylbenzoate 29 has also been used in another three-component synthesis along with amines 2 and ketones 31 (Scheme 8) [82]. This Mannich/lactamization reaction achieves good yields for a broad scope of 3-substituted isoindolinones 32, in either catalyst-free conditions or using p-toluenesulfonic acid. Ortho
- reaction of trimethylsilylaryltriflates 77, isocyanides 42 and CO2 (78). Plausible mechanism for the three-component synthesis of phthalimides 79. Copper-catalysed three-component reaction of 2-formylbenzonitriles 85, arenes 86 and diaryliodonium salts 87. Copper-catalysed three-component reaction of 2
Graphical Abstract
Figure 1: γ-Lactam-derived structures considered in this review.
Figure 2: Alkaloids containing an isoindolinone moiety.
Figure 3: Alkaloids containing the 2-oxindole ring system.
Figure 4: Drugs and biological active compounds containing an isoindolinone moiety.
Figure 5: Drugs and biologically active compounds bearing a 2-oxindole skeleton.
Scheme 1: Three-component reaction of benzoic acid 1, amides 2 and DMSO (3).
Scheme 2: Copper-catalysed three-component reaction of 2-iodobenzoic acids 10, alkynylcarboxylic acids 11 and...
Scheme 3: Proposed mechanism for the formation of methylene isoindolinones 13.
Scheme 4: Copper-catalysed three-component reaction of 2-iodobenzamide 17, terminal alkyne 18 and pyrrole or ...
Scheme 5: Palladium-catalysed three-component reaction of ethynylbenzamides 21, secondary amines 22 and CO (23...
Scheme 6: Proposed mechanism for the formation of methyleneisoindolinones 24.
Scheme 7: Copper-catalysed three-component reaction of formyl benzoate 29, amines 2 and alkynes 18.
Scheme 8: Copper-catalysed three-component reaction of formylbenzoate 29, amines 2 and ketones 31.
Scheme 9: Non-catalysed (A) and phase-transfer catalysed (B) three-component reactions of formylbenzoic acids ...
Scheme 10: Proposed mechanism for the formation of isoindolinones 36.
Scheme 11: Three-component reaction of formylbenzoic acid 33, amines 2 and fluorinated silyl ethers 39.
Scheme 12: Three-component Ugi reaction of 2-formylbenzoic acid (33), diamines 41 and isocyanides 42.
Scheme 13: Non-catalysed (A, B) and chiral phosphoric acid promoted (C) three-component Ugi reactions of formy...
Scheme 14: Proposed mechanism for the enantioselective formation of isoindolinones 46.
Scheme 15: Three-component reaction of benzoic acids 33 or 54, amines 2 and TMSCN (52).
Scheme 16: Several variations of the three-component reaction of formylbenzoic acids 33, amines 2 and isatoic ...
Scheme 17: Proposed mechanism for the synthesis of isoindoloquinazolinones 57.
Scheme 18: Three-component reaction of isobenzofuranone 61, amines 2 and isatoic anhydrides 56.
Scheme 19: Palladium-catalysed three-component reaction of 2-aminobenzamides 59, 2-bromobenzaldehydes 62 and C...
Scheme 20: Proposed mechanism for the palladium-catalysed synthesis of isoindoloquinazolinones 57.
Scheme 21: Four-component reaction of 2-vinylbenzoic acids 67, aryldioazonium tetrafluoroborates 68, DABCO·(SO2...
Scheme 22: Plausible mechanism for the formation of isoindolinones 71.
Scheme 23: Three-component reaction of trimethylsilylaryltriflates 77, isocyanides 42 and CO2 (78).
Scheme 24: Plausible mechanism for the three-component synthesis of phthalimides 79.
Scheme 25: Copper-catalysed three-component reaction of 2-formylbenzonitriles 85, arenes 86 and diaryliodonium...
Scheme 26: Copper-catalysed three-component reaction of 2-formylbenzonitriles 85, diaryliodonium salts 87 and ...
Scheme 27: Proposed mechanism for the formation of 2,3-diarylisoindolinones 88, 89 and 92.
Scheme 28: Palladium-catalysed three-component reaction of chloroquinolinecarbaldehydes 97 with isocyanides 42...
Scheme 29: Palladium-catalysed three-component reaction of imines 99 with CO (23) and ortho-iodoarylimines 100....
Scheme 30: Palladium-catalysed three-component reaction of amines 2 with CO (23) and aryl iodide 105.
Scheme 31: Three-component reaction of 2-ethynylanilines 109, perfluoroalkyl iodides 110 and carbon monoxide (...
Scheme 32: Ultraviolet-induced three-component reaction of N-(2-iodoaryl)acrylamides 113, DABCO·(SO2)2 (69) an...
Scheme 33: Proposed mechanism for the preparation of oxindoles 115.
Scheme 34: Three-component reaction of acrylamide 113, CO (23) and 1,4-benzodiazepine 121.
Scheme 35: Multicomponent reaction of sulfonylacrylamides 123, aryldiazonium tetrafluoroborates 68 and DABCO·(...
Scheme 36: Proposed mechanism for the preparation of oxindoles 124.
Scheme 37: Three-component reaction of N-arylpropiolamides 128, aryl iodides 129 and boronic acids 130.
Scheme 38: Proposed mechanism for the formation of diarylmethylene- and diarylallylideneoxindoles 131 and 132.
Scheme 39: Three-component reaction of cyclohexa-1,3-dione (136), amines 2 and alkyl acetylenedicarboxylates 1...
Scheme 40: Proposed mechanism for the formation of 2-oxindoles 138.
A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles
- Alexei Lukin,
- Anna Bakholdina,
- Anna Kryukova,
- Alexander Sapegin and
- Mikhail Krasavin
Beilstein J. Org. Chem. 2019, 15, 1061–1064, doi:10.3762/bjoc.15.103
- and the reaction of propargylureas 4 with primary amines studied in this work. Substrate scope for the three-component synthesis of 5. Plausible mechanism for the formation of 5. Catalyst screening results for the conversion of 4a to 5a. Supporting Information Supporting Information File 134: General
Graphical Abstract
Figure 1: Examples of imidazole (1 and 2) and oxazole (3) syntheses from propargylamides previously reported ...
Figure 2: Substrate scope for the three-component synthesis of 5.
Figure 3: Plausible mechanism for the formation of 5.
The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives
- Tilman Lechel,
- Roopender Kumar,
- Mrinal K. Bera,
- Reinhold Zimmer and
- Hans-Ulrich Reissig
Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61
- particular heterocyclic compounds. The synthesis of pyrimidines PM, pyrimidine N-oxides PO, oxazoles OX, 1,2-diketones DK and quinoxalines QU starting from β-ketoenamides KE is the topic of the present review. Review Scope of the LANCA three-component synthesis of β-ketoenamides The scope of the LANCA three
- -component synthesis of β-ketoenamides KE through the reaction of alkoxyallenes, nitriles and carboxylic acids is very broad and only a few clear limitations were found (Scheme 4). With lithiated methoxyallene (R1 = Me) – the standard alkoxyallene generally used to study new reactions – many conceivable
Graphical Abstract
Scheme 1: Discovery of the LANCA three-component reaction. The reaction of pivalonitrile (1) with lithiated m...
Scheme 2: Proposed mechanism of the LANCA three-component reaction to β-ketoenamides KE and pyridin-4-ol deri...
Scheme 3: One-pot preparation of pyridin-4-ols PY and their subsequent transformations to highly substituted ...
Scheme 4: Synthesis of β-ketoenamides KE by the LANCA three-component reaction of alkoxyallenes, nitriles and...
Scheme 5: β-Ketoenamides KE36–43 derived from enantiopure components.
Scheme 6: Bis-β-ketoenamides KE44–46 derived from aromatic dicarboxylic acids.
Scheme 7: Conversion of alkyl propargyl ethers E into aryl-substituted β-ketoenamides KEAr and selected produ...
Scheme 8: Condensation of LANCA-derived β-ketoenamides KE with ammonium salts to give 5-alkoxy-substituted py...
Scheme 9: Synthesis of PM31–35 from β-ketoenamides KE37, KE38, KE40, KE41 and KE78 obtained by method A (NH4O...
Scheme 10: Synthesis of bis-pyrimidine derivatives PM36, PM39 and PM40 from β-ketoenamides KE44–46 by method A...
Scheme 11: Functionalization of pyrimidine derivatives PM through selenium dioxide oxidations of PM5, PM9, PM15...
Scheme 12: Conversion of 2-vinyl-substituted pyrimidine PM7 into aldehyde PM50; (NMO = N-methylmorpholine N-ox...
Scheme 13: Deprotection of 5-alkoxy-substituted pyrimidines PM2, PM20 and PM29 and conversion into nonaflates ...
Scheme 14: Palladium-catalyzed coupling reactions of PM54 and PM12 giving rise to new pyrimidine derivatives P...
Scheme 15: Synthesis of pyrimidyl-substituted pyridyl nonaflate PM60.
Scheme 16: Condensation of LANCA-derived β-ketoenamides KE with hydroxylamine hydrochloride leading to pyrimid...
Scheme 17: Reactions of β-ketoenamides KE15 and KE7 with hydroxylamine hydrochloride leading to pyrimidine N-o...
Scheme 18: Structures of pyrimidine N-oxides PO30–33 derived from β-ketoenamides KE43, KE45, KE78 and KE80.
Scheme 19: Reduction of PO4 to PM5 and Boekelheide rearrangements of PO13, PO14, PO4 and PO30 to 4-acetoxymeth...
Scheme 20: Deprotection of 4-acetoxymethyl-substituted pyrimidine derivatives PM61 and PM63, oxidations to for...
Scheme 21: Synthesis of pyrimidinyl-substituted alkyne PM74 and conversion into furopyrimidine PM75 and Sonoga...
Scheme 22: Trifluoroacetic acid-promoted conversion of LANCA-derived β-ketoenamides KE into oxazoles OX and 1,...
Scheme 23: Conversion of β-ketoenamide KE79 into oxazole OX16 and transformation into 5-styryl-substituted oxa...
Scheme 24: Mechanisms of the formation of 1,2-diketones DK and of acetyl-substituted oxazole derivatives OX.
Scheme 25: Hydrogenolyses of benzyloxy-substituted β-ketoenamides KE52 and KE54 to 1,2-diketone DK14 and to di...
Scheme 26: Conversions of 2,4-dicyclopropyl-substituted oxazole OX7 into oxazole derivatives OX18–20 (PPA = po...
Scheme 27: Syntheses of vinyl and ethynyl-substituted oxazole derivatives OX21 and OX23 and their palladium-ca...
Scheme 28: Synthesis of C3-symmetric oxazole derivative OX28 and the STM current image of its 1-phenyloctane s...
Scheme 29: Condensation of 1,2-diketones DK with o-phenylenediamine to quinoxalines QU1–7 (CAN = cerium ammoni...
Scheme 30: The LANCA three-component reaction leading to β-ketoenamides KE and the structure of functionalized...
Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
- Rodrigo Abonia,
- Luisa F. Gutiérrez,
- Braulio Insuasty,
- Jairo Quiroga,
- Kenneth K. Laali,
- Chunqing Zhao,
- Gabriela L. Borosky,
- Samantha M. Horwitz and
- Scott D. Bunge
Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60
- State University, Kent, OH 44242, USA 10.3762/bjoc.15.60 Abstract A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone
- /HPF6 and studied by NMR and by DFT and GIAO-DFT. Keywords: model heteroarylmethylium salts; multicomponent; one-pot catalyst-free assembly; pharmacophoric triads; three-component synthesis; tris(heteroaryl)methanes; Yonemitsu-type reaction; Introduction During the last few decades multicomponent
- the indole and coumarin partners also characterizes these approaches, Scheme 2. Continuing our current program on the synthesis of quinoline-based heterocyclic compounds of biological interest [54][55][56][57], we describe here a Yonemitsu-based direct and reproducible three-component synthesis of
Graphical Abstract
Scheme 1: Representative examples of tris(hetero/aryl)methanes, molecular hybrids and bis(indolyl)methanes wi...
Scheme 2: Previous synthetic approaches for the synthesis of triarylmethane analogues in comparison to the pr...
Scheme 3: Synthesis of the starting N-alkylindoles 1{4–10}.
Scheme 4: General procedure for the synthesis of the starting quinoline-/quinolone aldehydes 6{1–7}.
Scheme 5: Chemset of coumarins 7{1–4} for elaboration in the MCR experiments.
Scheme 6: Exploratory reaction leading to isolation of products 8{1,1,1} and 9{1,1,1}.
Figure 1: Pseudo-three-component synthesis of bisindole triads 8 employing quinoline-/quinolone-CHO 6{1–6}, c...
Scheme 7: Chemset of further aldehydes 6{8–10} for elaboration in the MCR experiments.
Figure 2: Three-component synthesis of tris(heteroaryl)methane triads 9. aThis product was obtained as an ins...
Figure 3: Thermal ellipsoid plot (40% probability level) of the tris(heteroaryl)methane triad 9{4,7,1}.
Figure 4: DFT-optimized structure of 9{4,7,1} triad.
Scheme 8: Synthesis of crowed (Het12Het2/Ar2)C+PF6− salts 10.
Figure 5: 1D- and 2D-based NMR assignments for methylium-PF6 salt 10{4,4,8}.
Figure 6: 1D- and 2D-based NMR assignments for methylium-PF6 salt 10{4,4,11}.
Figure 7: Optimized geometry of methylium-PF6 salts 10{4,4,8}.
Figure 8: Optimized geometry of methylium-PF6 salt 10{4,4,11}.
An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes
- Hashem Sharghi,
- Pezhman Shiri and
- Mahdi Aberi
Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253
- cations. The 1H NMR spectrum displayed all protons of two -NMe2 groups as a singlet in the region of 3–3.2 ppm. On the other hand, the carbon chemical shift of C=N appeared around 134.7 ppm and 119.9 ppm attributed to two types of the chemical environment of the C=N carbon [46]. The three-component
- synthesis of tetrahydrobenzo[a]xanthenone derivatives 48a and the four component synthesis of tetrahydrobenzo[a]acridinone derivatives 48b were performed with good to excellent yields under solvent-free conditions at 75–85 °C within short reaction times using the higher acidic/stable ILs containing
Graphical Abstract
Figure 1: Different types of sulfonated materials as acid catalysts.
Scheme 1: Synthetic route of 3-methyl-1-sulfo-1H-imidazolium metal chloride ILs and their catalytic applicati...
Scheme 2: Synthetic route of 1,3-disulfo-1H-imidazolium transition metal chloride ILs and their catalytic app...
Scheme 3: Synthetic route of 1,3-disulfoimidazolium carboxylate ILs and their catalytic applications in the s...
Scheme 4: Synthetic route of [BiPy](HSO3)2Cl2 and [Dsim]HSO4 ILs and their catalytic applications for the syn...
Scheme 5: The catalytic applications of (C4(DABCO-SO3H)2·4Cl) IL for the synthesis of spiro-isatin derivative...
Scheme 6: The catalytic applications of (C4(DABCO-SO3H)2·4Cl) IL for the synthesis of bis 2-amino-4H-pyran de...
Scheme 7: The synthetic route of N,N-disulfo-1,1,3,3-tetramethylguanidinium carboxylate ILs and their catalyt...
Scheme 8: The catalytic application of 1-methyl-3-sulfo-1H-imidazolium tetrachloroferrate IL in the synthesis...
Scheme 9: The synthetic route of 3-sulfo-1H-imidazolopyrimidinium hydrogen sulfate IL and its catalytic appli...
Scheme 10: The results for the synthesis of bis(indolyl)methanes and di(bis(indolyl)methyl)benzenes in the pre...
Scheme 11: The catalytic applications of 1-(1-sulfoalkyl)-3-methylimidazolium chloride acidic ILs for the hydr...
Scheme 12: The synthetic route of immobilized 1,4-diazabicyclo[2.2.2]octanesulfonic acid chloride on SiO2 and ...
Scheme 13: The catalytic application of a silica-bonded sulfoimidazolium chloride for the synthesis of 12-aryl...
Scheme 14: The synthetic route of the SBA-15-Ph-SO3H and its catalytic applications for the synthesis of 2H-in...
Scheme 15: The synthetic route for heteropolyanion-based ionic liquids immobilized on mesoporous silica SBA-15...
Scheme 16: Some mechanism aspects of SSA catalyst for the protection of amine derivatives.
Scheme 17: The synthetic route for MWCNT-SO3H and its catalytic application for the synthesis of N-substituted...
Scheme 18: The sulfonic acid-functionalized polymers (P-SO3H) covalently grafted on multi-walled carbon nanotu...
Scheme 19: The transesterification reaction in the presence of S-MWCNTs.
Scheme 20: The synthetic route for the new hypercrosslinked supermicroporous polymer via the Friedel–Crafts al...
Scheme 21: The synthetic route for a new microporous copolymer via the Friedel–Crafts alkylation reaction of t...
Scheme 22: The synthetic route for sulfonated polynaphthalene and its catalytic application for the amidoalkyl...
Scheme 23: The synthetic route of the acidic carbon material and its catalytic application in the etherificatio...
Scheme 24: The synthetic route of the acidic carbon materials and their catalytic applications for the esterif...
Scheme 25: The sulfonated MWCNTs.
Scheme 26: The sulfonated nanoscaled diamond powder for the dehydration of D-xylose into furfural.
Scheme 27: The synthetic route and catalytic application of the GR-SO3H.
5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines
- Ranjana Aggarwal and
- Suresh Kumar
Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15
Graphical Abstract
Figure 1: Selected examples of drugs with fused pyrazole rings.
Figure 2: Typical structures of some fused pyrazoloazines from 5-aminopyrazoles.
Scheme 1: Regiospecific synthesis of 4 and 6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines.
Scheme 2: Synthesis of pyrazolo[3,4-b]pyridine-6-carboxylates.
Scheme 3: Synthesis of 1,4,6-triaryl-1H-pyrazolo[3,4-b]pyridines with ionic liquid .
Scheme 4: Synthesis of coumarin-based isomeric tetracyclic pyrazolo[3,4-b]pyridines.
Scheme 5: Synthesis of 6-substituted pyrazolo[3,4-b]pyridines under Heck conditions.
Scheme 6: Microwave-assisted palladium-catalyzed synthesis of pyrazolo[3,4-b]pyridines.
Scheme 7: Acid-catalyzed synthesis of pyrazolo[3,4-b]pyridines via enaminones.
Scheme 8: Synthesis of pyrazolo[3,4-b]pyridines via aza-Diels–Alder reaction.
Scheme 9: Synthesis of macrocyclane fused pyrazolo[3,4-b]pyridine derivatives.
Scheme 10: Three-component synthesis of 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine derivatives.
Scheme 11: Ultrasonicated synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-diones.
Scheme 12: Synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine] derivatives under conventional heating co...
Scheme 13: Nanoparticle-catalyzed synthesis of pyrazolo[3,4-b]pyridine-spiroindolinones.
Scheme 14: Microwave-assisted multicomponent synthesis of spiropyrazolo[3,4-b]pyridines.
Scheme 15: Unexpected synthesis of naphthoic acid-substituted pyrazolo[3,4-b]pyridines.
Scheme 16: Multicomponent synthesis of variously substituted pyrazolo[3,4-b]pyridine derivatives.
Scheme 17: Three-component synthesis of 4,7-dihydropyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyridines.
Scheme 18: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanediones.
Scheme 19: Ultrasound-mediated three-component synthesis of pyrazolo[3,4-b]pyridines.
Scheme 20: Multicomponent synthesis of 4-aryl-3-methyl-1-phenyl-4,6,8,9-tetrahydropyrazolo [3,4-b]thiopyrano[4...
Scheme 21: Synthesis of 2,3-dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones.
Scheme 22: FeCl3-catalyzed synthesis of o-hydroxyphenylpyrazolo[3,4-b]pyridine derivatives.
Scheme 23: Ionic liquid-mediated synthesis of pyrazolo[3,4-b]pyridines.
Scheme 24: Microwave-assisted synthesis of pyrazolo[3,4-b]pyridines.
Scheme 25: Multicomponent synthesis of pyrazolo[3,4-b]pyridine-5-carbonitriles.
Scheme 26: Unusual domino synthesis of 4,7-dihydropyrazolo[3,4-b]pyridine-5-nitriles.
Scheme 27: Synthesis of 4,5,6,7-tetrahydro-4H-pyrazolo[3,4-b]pyridines under conventional heating and ultrasou...
Scheme 28: L-Proline-catalyzed synthesis of of pyrazolo[3,4-b]pyridine.
Scheme 29: Microwave-assisted synthesis of 5-aminoarylpyrazolo[3,4-b]pyridines.
Scheme 30: Microwave-assisted multi-component synthesis of pyrazolo[3,4-e]indolizines.
Scheme 31: Synthesis of fluoropropynyl and fluoroalkyl substituted pyrazolo[1,5-a]pyrimidine.
Scheme 32: Acid-catalyzed synthesis of pyrazolo[1,5-a]pyrimidine derivatives.
Scheme 33: Chemoselective and regiospecific synthesis of 2-(3-methylpyrazol-1’-yl)-5-methylpyrazolo[1,5-a]pyri...
Scheme 34: Regioselective synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidines.
Scheme 35: Microwave-assisted synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidine carboxylates.
Scheme 36: Microwave and ultrasound-assisted synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidines.
Scheme 37: Base-catalyzed unprecedented synthesis of pyrazolo[1,5-a]pyrimidines via C–C bond cleavage.
Scheme 38: Synthesis of aminobenzothiazole/piperazine linked pyrazolo[1,5-a]pyrimidines.
Scheme 39: Synthesis of aminoalkylpyrazolo[1,5-a]pyrimidine-7-amines.
Scheme 40: Synthesis of pyrazolo[1,5-a]pyrimidines from condensation of 5-aminopyrazole 126 and ethyl acetoace...
Scheme 41: Synthesis of 7-aminopyrazolo[1,5-a]pyrimidines.
Scheme 42: Unexpected synthesis of 7-aminopyrazolo[1,5-a]pyrimidines under solvent free and solvent-mediated c...
Scheme 43: Synthesis of N-(4-aminophenyl)-7-aryloxypyrazolo[1,5-a]pyrimidin-5-amines.
Scheme 44: Base-catalyzed synthesis of 5,7-diarylpyrazolo[1,5-a]pyrimidines.
Scheme 45: Synthesis of 6,7-dihydropyrazolo[1,5-a]pyrimidines in PEG-400.
Scheme 46: Synthesis of 7-heteroarylpyrazolo[1,5-a]pyrimidine-3-carboxamides.
Scheme 47: Synthesis of 7-heteroarylpyrazolo[1,5-a]pyrimidine derivatives under conventional heating and micro...
Scheme 48: Synthesis of N-aroylpyrazolo[1,5-a]pyrimidine-5-amines.
Scheme 49: Regioselective synthesis of ethyl pyrazolo[1,5-a]pyrimidine-7-carboxylate.
Scheme 50: Sodium methoxide-catalyzed synthesis of 3-cyano-6,7-diarylpyrazolo[1,5-a]pyrimidines.
Scheme 51: Synthesis of various pyrazolo[3,4-d]pyrimidine derivatives.
Scheme 52: Synthesis of hydrazinopyrazolo[3,4-d]pyrimidine derivatives.
Scheme 53: Synthesis of N-arylidinepyrazolo[3,4-d]pyrimidin-5-amines.
Scheme 54: Synthesis of pyrazolo[3,4-d]pyrimidinyl-4-amines.
Scheme 55: Iodine-catalyzed synthesis of pyrazolo[3,4-d]pyrimidinones.
Scheme 56: Synthesis of ethyl 6-amino-2H-pyrazolo[3,4-d]pyrimidine-4-carboxylate.
Scheme 57: Synthesis of 4-substituted-(3,6-dihydropyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidines.
Scheme 58: Synthesis of 1-(2,4-dichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl carboxamides.
Scheme 59: Synthesis of 5-(1,3,4-thidiazol-2-yl)pyrazolo[3,4-d]pyrimidine.
Scheme 60: One pot POCl3-catalyzed synthesis of 1-arylpyrazolo[3,4-d]pyrimidin-4-ones.
Scheme 61: Synthesis of 4-amino-N1,C3-dialkylpyrazolo[3,4-d]pyrimidines under Suzuki conditions.
Scheme 62: Microwave-assisted synthesis of pyrazolo[3,4-b]pyrazines.
Scheme 63: Synthesis and derivatization of pyrazolo[3,4-b]pyrazine-5-carbonitriles.
Scheme 64: Synthesis of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones.
Scheme 65: Synthesis of 2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one.
Scheme 66: Synthesis of pyrazolo[1,5-a][1,3,5]triazine-8-carboxylic acid ethyl ester.
Scheme 67: Microwave-assisted synthesis of 4,7-dihetarylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 68: Alternative synthetic route to 4,7-diheteroarylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 69: Synthesis of 4-aryl-2-ethylthio-7-methylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 70: Microwave-assisted synthesis of 4-aminopyrazolo[1,5-a][1,3,5]triazine.
Scheme 71: Synthesis of pyrazolo[3,4-d][1,2,3]triazines from pyrazol-5-yl diazonium salts.
Scheme 72: Synthesis of 2,5-dihydropyrazolo[3,4-e][1,2,4]triazines.
Scheme 73: Synthesis of pyrazolo[5,1-c][1,2,4]triazines via diazopyrazolylenaminones.
Scheme 74: Synthesis of pyrazolo[5,1-c][1,2,4]triazines in presence of sodium acetate.
Scheme 75: Synthesis of various 7-diazopyrazolo[5,1-c][1,2,4]triazine derivatives.
Scheme 76: One pot synthesis of pyrazolo[5,1-c][1,2,4]triazines.
Scheme 77: Synthesis of 4-amino-3,7,8-trinitropyrazolo-[5,1-c][1,2,4]triazines.
Scheme 78: Synthesis of tricyclic pyrazolo[5,1-c][1,2,4]triazines by azocoupling reaction.
One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids
- Melanie Denißen,
- Alexander Kraus,
- Guido J. Reiss and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231
- conditions are well-suited for concatenating the arylpropiolic anhydride formation, intramolecular cycloaddition and imidation in a one-pot fashion in the sense of a consecutive pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones 4, which was first probed with an electroneutral (1a
- -dihydro-1H-benzo[f]isoindolyl moiety in 6 are absolutely planar. Photophysical properties The pseudo three-component synthesis of 1H-benzo[f]isoindole-1,3(2H)-diones 4 furnishes a substance library with electronically diverse substitution patterns and already upon eyesight several derivatives are
- ]furan-1,3-diones 2 via in situ activation of arylpropiolic acids 1. Optimization of the synthesis of 2,4-diphenyl-1H-benzo[f]isoindole-1,3(2H)-dione (4a) by imidation of 4-phenylnaphtho[2,3-c]furan-1,3-dione (2a) with aniline (3a). Pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H
Graphical Abstract
Scheme 1: Mechanistic rationale and optimization of the domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-dio...
Scheme 2: Domino synthesis of 4-arylnaphtho[2,3-c]furan-1,3-diones 2 via in situ activation of arylpropiolic ...
Scheme 3: Optimization of the synthesis of 2,4-diphenyl-1H-benzo[f]isoindole-1,3(2H)-dione (4a) by imidation ...
Scheme 4: Pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones 4.
Scheme 5: Modified sequence for the synthesis of acceptor-substituted 4-aryl-1H-benzo[f]isoindole-1,3(2H)-dio...
Figure 1: The ORTEP-style plot of crystal structure 4b (ellipsoids are draw at the 40% probability level).
Scheme 6: Pseudo four-component synthesis of (E)-2,9-diphenyl-3-(phenylimino)-2,3-dihydro-1H-benzo[f]isoindol...
Scheme 7: Synthesis of 6-phenyl-12H-benzo[f]benzo[4,5]imidazo[2,1-a]isoindol-12-one (6).
Figure 2: The ORTEP-type plot of the crystal structure 5 (left) and a centrosymmetric dimer formation by π–π ...
Figure 3: The ORTEP-type plot of the asymmetric unit of the crystal structure 6 (top) and π-stacking interact...
Figure 4: Emission properties of compounds 4a,b,d–f, 5, and 6 under handheld UV-lamp (λexc ≈ 350 nm).
Figure 5: Relative emission intensities of compounds 4a,b,d–f (recorded in CH2Cl2 UVASOL® at T = 293 K; λexc ...
Figure 6: Absorption and emission properties of selected imides 4 measured in CH2Cl2 UVASOL® at 293 K with λe...
Figure 7: Hammett–Taft correlations of the emission maxima (red circles, lmax,em = 4274 · sR + 24495 [cm−1], R...
Figure 8: Relative emission intensities of the 1-phenyl-2,3-naphthaleneimide 4a (blue) and the pentacyclus 6 ...
Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides
- Lena Huck,
- Juan F. González,
- Elena de la Cuesta and
- J. Carlos Menéndez
Beilstein J. Org. Chem. 2016, 12, 1772–1777, doi:10.3762/bjoc.12.166
Graphical Abstract
Scheme 1: Summary of the work described in this paper.
Scheme 2: Synthesis of aziridines 2.
Figure 1: NOE effects in compound 2f.
Scheme 3: Mechanistic proposal accounting for the chemo- and diastereoselective formation of aziridines 2.
Scheme 4: Transformation of aziridines 2 into β-trifluoroacetamido-α-ketoamides 6.
Scheme 5: Two mechanistic proposals explaining the formation of compounds 6.
Scheme 6: Transformation of aziridines 2 into vicinal tricarbonyl compounds 11 and transformation of the latt...
Scheme 7: Mechanistic proposal for the transformation of aziridines 2 into compounds 11.
Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
- Mohammad Haji
Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121
- -phosphonates: A one-pot three-component synthesis of N-arylisoquinolone-1-phosphonates 119 through the Kabachnik–Fields reaction of ethyl 2-(2-formyl-4,5-dimethoxyphenyl)acetate (116) with anilines 117 and triethyl phosphite in the presence of trifluoroacetic acid as catalyst has been reported by Borse et al
- phosphonylpyrans 152, 154 and 156, respectively (Scheme 33). 3.2 Three-component synthesis of (2-amino-3-cyano-4H-chromen-4-yl)phosphonates Because of the widespread biological activities related to 2-amino-4H-chromene derivatives, the synthesis of (2-amino-3-cyano-4H-chromen-4-yl)phosphonates has attracted much
- synthesis of 2-oxoindolin-3-ylphosphonates. Intramolecular cyclization of phospha-Michael adducts to give dihydropyridinylphosphonates. Synthesis of fused phosphonylpyrans via intramolecular cyclization of phospha-Michael adducts. InCl3-catalyzed three-component synthesis of (2-amino-3-cyano-4H-chromen-4-yl
Graphical Abstract
Scheme 1: The Biginelli condensation.
Scheme 2: The Biginelli reaction of β-ketophosphonates catalyzed by ytterbium triflate.
Scheme 3: Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphona...
Scheme 4: Biginelli reaction of dialkyl (3,3,3-trifluoropropyl-2-oxo)phosphonate with trialkyl orthoformates ...
Scheme 5: p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.
Scheme 6: General Kabachnik–Fields reaction for the synthesis of α-aminophosphonates.
Scheme 7: Phthalocyanine–AlCl catalyzed Kabachnik–Fields reaction of N-Boc-piperidin-4-one with diethyl phosp...
Scheme 8: Kabachnik–Fields reaction of isatin with diethyl phosphite and benzylamine.
Scheme 9: Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid-catalyzed Kabachnik–Fields reaction of i...
Scheme 10: The Mg(ClO4)2-catalyzed Kabachnik–Fields reaction of 1-tosylpiperidine-4-one.
Scheme 11: An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylph...
Scheme 12: A classical Kabachnik–Fields reaction followed by an intramolecular ring-closing reaction for the s...
Scheme 13: Synthesis of (S)-piperidin-2-phosphonic acid through an asymmetric Kabachnik–Fields reaction.
Scheme 14: A modified diastereoselective Kabachnik–Fields reaction for the synthesis of isoindolin-1-one-3-pho...
Scheme 15: A microwave-assisted Kabachnik–Fields reaction toward isoindolin-1-ones.
Scheme 16: The synthesis of 3-arylmethyleneisoindolin-1-ones through a Horner–Wadsworth–Emmons reaction of Kab...
Scheme 17: An efficient one-pot method for the synthesis of ethyl (2-alkyl- and 2-aryl-3-oxoisoindolin-1-yl)ph...
Scheme 18: FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diet...
Scheme 19: Three-component reaction of 6-methyl-3-formylchromone (75) with hydrazine derivatives or hydroxylam...
Scheme 20: Three-component reaction of 6-methyl-3-formylchromone (75) with thiourea, guanidinium carbonate or ...
Scheme 21: Three-component reaction of 6-methyl-3-formylchromone (75) with 1,4-bi-nucleophiles in the presence...
Scheme 22: One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.
Scheme 23: Lewis acid–surfactant combined catalysts for the one-pot three-component reaction of 2-alkynylbenza...
Scheme 24: Lewis acid catalyzed cyclization of different Kabachnik–Fields adducts.
Scheme 25: Three-component synthesis of N-arylisoquinolone-1-phosphonates 119.
Scheme 26: CuI-catalyzed three-component tandem reaction of 2-(2-formylphenyl)ethanones with aromatic amines a...
Scheme 27: Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component re...
Scheme 28: FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.
Scheme 29: Synthesis of indole bisphosphonates through a modified Kabachnik–Fields reaction.
Scheme 30: Synthesis of heterocyclic bisphosphonates via Kabachnik–Fields reaction of triethyl orthoformate.
Scheme 31: A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.
Scheme 32: Intramolecular cyclization of phospha-Michael adducts to give dihydropyridinylphosphonates.
Scheme 33: Synthesis of fused phosphonylpyrans via intramolecular cyclization of phospha-Michael adducts.
Scheme 34: InCl3-catalyzed three-component synthesis of (2-amino-3-cyano-4H-chromen-4-yl)phosphonates.
Scheme 35: Synthesis of phosphonodihydropyrans via a domino Knoevenagel/hetero-Diels–Alder process.
Scheme 36: Multicomponent synthesis of phosphonodihydrothiopyrans via a domino Knoevenagel/hetero-Diels–Alder ...
Scheme 37: One-pot four-component synthesis of 1,2-dihydroisoquinolin-1-ylphosphonates under multicatalytic co...
Scheme 38: CuI-catalyzed four-component reactions of methyleneaziridines towards alkylphosphonates.
Scheme 39: Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its p...
Scheme 40: Copper(I)-catalyzed three-component reaction towards 1,2,3-triazolyl-5-phosphonates.
Scheme 41: Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to aff...
Scheme 42: Synthesis of (4-imino-3,4-dihydroquinazolin-2-yl)phosphonates via an isocyanide-based three-compone...
Scheme 43: Silver-catalyzed three-component synthesis of (2-imidazolin-4-yl)phosphonates.
Scheme 44: Three-component synthesis of phosphonylpyrazoles.
Scheme 45: One-pot three-component synthesis of 3-carbo-5-phosphonylpyrazoles.
Scheme 46: A one-pot two-step method for the synthesis of phosphonylpyrazoles.
Scheme 47: A one-pot method for the synthesis of (5-vinylpyrazolyl)phosphonates.
Scheme 48: Synthesis of 1H-pyrrol-2-ylphosphonates via the [3 + 2] cycloaddition of phosphonate azomethine yli...
Scheme 49: Three-component synthesis of 1H-pyrrol-2-ylphosphonates.
Scheme 50: The classical Reissert reaction.
Scheme 51: One-pot three-component synthesis of N-phosphorylated isoquinolines.
Scheme 52: One-pot three-component synthesis of 1-acyl-1,2-dihydroquinoline-2-phosphonates and 2-acyl-1,2-dihy...
Scheme 53: Three-component reaction of pyridine derivatives with ethyl propiolate and dialkyl phosphonates.
Scheme 54: Three-component reactions for the phosphorylation of benzothiazole and isoquinoline.
Scheme 55: Three-component synthesis of diphenyl [2-(aminocarbonyl)- or [2-(aminothioxomethyl)-1,2-dihydroisoq...
Scheme 56: Three-component stereoselective synthesis of 1,2-dihydroquinolin-2-ylphosphonates and 1,2-dihydrois...
Scheme 57: Diphosphorylation of diazaheterocyclic compounds via a tandem 1,4–1,2 addition of dimethyl trimethy...
Scheme 58: Multicomponent reaction of alkanedials, acetamide and acetyl chloride in the presence of PCl3 and a...
Scheme 59: An oxidative domino three-component synthesis of polyfunctionalized pyridines.
Scheme 60: A sequential one-pot three-component synthesis of polysubstituted pyrroles.
Scheme 61: Three-component decarboxylative coupling of proline with aldehydes and dialkyl phosphites for the s...
Scheme 62: Three-component domino aza-Wittig/phospha-Mannich sequence for the phosphorylation of isatin deriva...
Scheme 63: Stereoselective synthesis of phosphorylated trans-1,5-benzodiazepines via a one-pot three-component...
Scheme 64: One-pot three-component synthesis of phosphorylated 2,6-dioxohexahydropyrimidines.
C–H bond halogenation catalyzed or mediated by copper: an overview
- Wenyan Hao and
- Yunyun Liu
Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230
- . CuI-mediated synthesis of iododibenzo[b,d]furans via C–H functionalization. Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation. Copper-catalyzed halogenations of 2-amino-1,3thiazoles. Copper-mediated chlorination and bromination of indolizines. Copper-catalyzed three-component synthesis
Graphical Abstract
Scheme 1: Copper-catalyzed C–H bond halogenation of 2-arylpyridine.
Scheme 2: ortho-Chlorination of 2-arylpridines with acyl chlorides.
Scheme 3: Copper-catalyzed chlorination of 2-arylpyridines using LiCl.
Scheme 4: Copper-catalyzed C–H halogenation of 2-arylpyridines using LiX.
Scheme 5: Copper-mediated selective C–H halogenations of 2-arylpyridine.
Scheme 6: Copper-catalyzed C–H o-halogenation using removable DG.
Scheme 7: Copper-catalyzed C–H halogenations using PIP as DG.
Scheme 8: Copper-catalyzed quinoline C–H chlorination.
Scheme 9: Copper-catalyzed arene C–H fluorination of benzamides.
Scheme 10: Copper-catalyzed arene C–H iodination of 1,3-azoles.
Scheme 11: Copper-catalyzed C–H halogenations of phenols.
Scheme 12: Proposed mechanism for the C–H halogenation of phenols.
Scheme 13: Copper-catalyzed halogenation of electron enriched arenes.
Scheme 14: Copper-catalyzed C–H bromination of arenes.
Scheme 15: CuI-mediated synthesis of iododibenzo[b,d]furans via C–H functionalization.
Scheme 16: Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation.
Scheme 17: Copper-catalyzed halogenations of 2-amino-1,3thiazoles.
Scheme 18: Copper-mediated chlorination and bromination of indolizines.
Scheme 19: Copper-catalyzed three-component synthesis of bromoindolizines.
Scheme 20: Copper-mediated C–H halogenation of azacalix[1]arene[3]pyridines.
Scheme 21: Copper-mediated cascade synthesis of halogenated pyrrolones.
Scheme 22: Copper-mediated alkene C–H chlorination in spirothienooxindole.
Scheme 23: Copper-catalyzed remote C–H chlorination of alkyl hydroperoxides.
Scheme 24: Copper-catalyzed C–H fluorination of alkanes.
Scheme 25: Copper-catalyzed or mediated C–H halogenations of active C(sp3)-bonds.
Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
- Pavel K. Mykhailiuk
Beilstein J. Org. Chem. 2015, 11, 16–24, doi:10.3762/bjoc.11.3
Graphical Abstract
Figure 1: Bioactive compounds and agrochemicals with fluorinated pyrazoles.
Figure 2: Bioactive compounds with C2F5 group [34-36].
Figure 3: X-ray crystal structure of pyrazoles 10a, 19b and 20b [50].
Figure 4: Structure of the expected product 19a, and the observed isomeric one – 19b.
Scheme 1: Comparison of CF3CHN2 vs C2F5CHN2 in the reaction with alkyne 19.
Scheme 2: Synthesis of 3,4-disubstituted pyrazole 24.
Scheme 3: Synthesis of C2F5-substituted acids 25 and 27. In brackets are the known bioactive compounds DP-23, ...
Multicomponent reactions in nucleoside chemistry
- Mariola Koszytkowska-Stawińska and
- Włodzimierz Buchowicz
Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179
- activity (IC50 = 1.4 ± 0.1 µM) [42]. Anti-leishmanian activities of the 7-substituted derivatives of compound 65 were also given [42]. Details concerning the preparation of those compounds were not given. The three-component synthesis of compounds 69 and 70 developed by Zhang et al. involved the
Graphical Abstract
Figure 1: Selected chemical modifications of natural ribose or 2'-deoxyribose nucleosides leading to the deve...
Scheme 1: (a) Classical Mannich reaction; (b) general structures of selected hydrogen active components and s...
Scheme 2: Reagents and reaction conditions: i. H2O or H2O/EtOH, 60–100 °C, 7 h–10 d; ii. H2, Pd/C or PtO2; ii...
Scheme 3: Reagents and reaction conditions: i. H2O, 90 °C, overnight.
Scheme 4: Reagents and reaction conditions: i. AcOH, H2O, 60 °C, 12 h-5 d; ii. AcOH, H2O, 60 °C, 8 h.
Scheme 5: Reagents and reaction conditions: i. CuBr, THF, reflux, 0.5 h; ii. n-Bu4NF·3H2O, THF, rt, 2 h.
Scheme 6: Reagents and reaction conditions: i. [bmim][PF6], 80 °C, 5–8 h.
Scheme 7: Reagents and reaction conditions: i. EtOH, reflux, 24 h.
Scheme 8: Reagents and reaction conditions: i. NaOAc, H2O, 95 °C, 1–16 h; ii. NaOAc, H2O, 95 °C, 1 h.
Scheme 9: Reagents and reaction conditions: i. a. 37% aq HCl, MeOH; b. NaOAc, 1,4-dioxane, H2O, 100 °C, overn...
Scheme 10: Reagents and reaction conditions: i. DMAP, DCC, MeOH, rt, 1 h.
Scheme 11: The Kabachnik–Fields reaction.
Scheme 12: Reagents and reaction conditions: i. 60 °C, 3 h; ii. 80 °C, 2 h.
Scheme 13: The four-component Ugi reaction.
Scheme 14: Reagents and reaction conditions: i. MeOH, rt, 2–3 d, yields not given.
Scheme 15: Reagents and reaction conditions: i. MeOH/CH2Cl2 (1:1), rt, 24 h, yield not given; ii. 6 N aq HCl, ...
Scheme 16: Reagents and reaction conditions: i. MeOH/H2O, rt, 26 h; ii. aq AcOH, reflux, 50%; iii. reversed ph...
Scheme 17: Reagents and reaction conditions: i. MeOH, rt, 24 h; ii. HCl, MeOH, 0 °C to rt, 6 h, then H2O, rt, ...
Scheme 18: Reagents and reaction conditions: i. DMF/Py/MeOH (1:1:1), rt, 48 h; ii. 10% HCl/MeOH, rt, 30 min.
Scheme 19: Reagents and reaction conditions (R = CH3 or H): i. CH2Cl2/MeOH (2:1), 35–40 °C, 2 d; ii. HF/pyridi...
Scheme 20: Reagents and reaction conditions: i. MeOH, 76%; ii. 80% aq TFA, 100%.
Scheme 21: Reagents and reaction conditions: i. EtOH, rt, 72 h; ii. Zn, aq NaH2PO4, THF, rt, 1 week; then 80% ...
Scheme 22: Reagents and reaction conditions: i. EtOH, rt, 48 h, then silica gel chromatography, 33% for 57 (30...
Scheme 23: Reagents and reaction conditions: i. [bmim]BF4, 80 °C, 4 h; ii. [bmim]BF4, 80 °C, 3 h; iii. [bmim]BF...
Scheme 24: Reagents and reaction conditions: i. [bmim]BF4, 80 °C.
Scheme 25: Reagents and reaction conditions: i. H3PW12O40 (2 mol %), EtOH, 50 °C, 2–15 h; ii. H3PW12O40 (2 mol...
Scheme 26: General scheme of the Biginelli reaction.
Scheme 27: Reagents and reaction conditions: i. EtOH, reflux.
Scheme 28: Reagents and reaction conditions: i. Bu4N+HSO4−, diethylene glycol, 120 °C, 1.5–3 h.
Scheme 29: Reagents and reaction conditions: i. BF3·Et2O, CuCl, AcOH, THF, 65 °C, 24 h; ii. Yb(OTf)3, THF, ref...
Scheme 30: Reagents and reaction conditions: TCT (10 mol %), rt: i. 100 min; ii. 150 min; iii. 140 min.
Scheme 31: Reagents and reaction conditions: i. EtOH, microwave irradiation (300 W), 10 min; ii. EtOH, 75 °C, ...
Scheme 32: The Hantzsch reaction.
Scheme 33: Reagents and reaction conditions: TCT (10 mol %), rt, 80–150 min.
Scheme 34: Reagents and reaction conditions: i. Yb(OTf)3, THF, 90 °C, 12 h; ii. 4 Å molecular sieves, EtOH, 90...
Scheme 35: Reagents and reaction conditions: i. MeOH, 50 °C, 48 h.
Scheme 36: Reagents and reaction conditions: i. MeOH, 25 °C, 5 d.
Scheme 37: Bu4N+HSO4−, diethylene glycol, 80 °C, 1–2 h.
Scheme 38: The three-component carbopalladation of dienes on the example of buta-1,3-diene.
Scheme 39: Reagents and reaction conditions: i. 5 mol % Pd(dba)2, Bu4NCl, ZnCl2, acetonitrile or DMSO, 80 °C o...
Scheme 40: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 41: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 42: The three-component Bucherer–Bergs reaction.
Scheme 43: Reagents and reaction conditions: i. MeOH, H2O, 70 °C, 4.5 h; ii. (1) H2, 5% Pd/C, MeOH, 55 °C, 5 h...
Scheme 44: Reagents and reaction conditions: i. pyridine, MgSO4, 100 °C, 28 h, N2; ii. DMF, 70–90 °C, 22–30 h,...
Scheme 45: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (600 W), 6–10...
Scheme 46: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (560 W), 6–10...
Scheme 47: Reagents and reaction conditions: i. CeCl3·7H2O (20 mol %), NaI (20 mol %), microwave irradiation (...
Scheme 48: Reagents and reaction conditions: i. PhI(OAc)2 (3 mol %), microwave irradiation (45 °C), 6–9 min.
Scheme 49: Reagents and reaction conditions: i. 117, ethyl pyruvate, TiCl4, dichloromethane, −78 °C, 1 h; then ...
Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles
- Yogesh Kumar,
- Vijay Bahadur,
- Anil K. Singh,
- Virinder S. Parmar,
- Erik V. Van der Eycken and
- Brajendra K. Singh
Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145
- : benzimidazole; Cu(I) catalysis; microwave-assisted synthesis; multicomponent; three component synthesis; Introduction Due to their structural range and biological importance nitrogen-containing heterocycles have been striking targets for many years. They are found in a variety of natural products and are
Graphical Abstract
Scheme 1: Synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles.
Scheme 2: Plausible mechanism for the synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-b...
A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids
- Natalia V. Pavlenko,
- Tatiana I. Oos,
- Yurii L. Yagupolskii,
- Igor I. Gerus,
- Uwe Doeller and
- Lothar Willms
Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66
- , dioxane, 100 °C, 3 h, argon atmosphere, yield 10 ~90%. Three-component synthesis of CF3 containing α-aminophosphinic acids 14a,b. Reagents and conditions: i) An equimolar mixture of acid 1, dibenzylamine, HCl and two fold excess of aldehyde, H2O, 80 °C, 3 h; isolated yields: 13a (52%), 13b (28%); yields
Graphical Abstract
Scheme 1: Synthesis of (trifluoromethyl)phosphinic acid (1) and ethyl and isopropyl esters 2–4. Reagents and ...
Scheme 2: Three-component Kabachnik–Fields reaction of CF3(H)P(O)(OiPr) (2) with formaldehyde and dibenzylami...
Scheme 3: Three-component synthesis of CF3 containing α-aminophosphinic acids 14a,b. Reagents and conditions:...
Scheme 4: Interaction of the acid 1 with tert-butyl benzylidenecarbamate (21). Reagents and conditions: i) an...
Scheme 5: Interaction of the acids 1 and 6 with ethyl 2-[(tert-butoxycarbonyl)imino]acetate (22). Reagents an...
Scheme 6: Transformation of the ester 24 into the appropriate free acid 25. Reagents and conditions: i) two f...
Scheme 7: Reaction of the acids (1) and (6) with methyl 2-imino-3-methylbutanoate (26). Reagents and conditio...
Scheme 8: Interaction of the acid 1 with ethyl 2-(tert-butoxycarbonylamino)acrylate (29). Reagents and condit...
Scheme 9: Interaction of a mixture of the esters 3 and 4 with 2-acetamidoacrylic acid (33). Reagents and cond...
Scheme 10: Interaction of a mixture of the acid 1 with diethyl acetaminomethylenemalonate (38). Reagents and c...
One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines
- Christian Muschelknautz,
- Robin Visse,
- Jan Nordmann and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51
- particular, the electrophilic enyne intermediate [32][40], which is trespassed in the three-component synthesis of solid-state luminescent push–pull indolones 4, intrigued our interest for accessing even triene push–pull systems and to study their electronic properties. Here we report our findings on the
- diversity-oriented and highly selective three-component synthesis of a new class of deeply colored triene merocyanines in a one-pot fashion. Furthermore, their absorption and emission characteristics are investigated. Results and Discussion After the coupling of the N-methyl-substituted alkynoyl o
- the dropcasted film (left trace) (recorded at room temperature, normalized spectrum). DFT-computed (B3LYP functional, 6-311G(d,p) basis set) FMOs (HOMO, bottom; LUMO (center), and LUMO+2 (top)) of merocyanine 2E,4Z,6Z-10a. Three-component synthesis of 1-styryleth-2-enylideneindolones 8. Three
Graphical Abstract
Figure 1: Linear push–pull solid-state diene lumophores with conformationally flexible and fixed acceptor moi...
Scheme 1: Three-component synthesis of 1-styryleth-2-enylideneindolones 8.
Figure 2: DFT-computed energy differences of the stereoisomers of 2Z,4Z-8a and 2Z,4E-8a.
Scheme 2: Three-component synthesis of 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones 10.
Figure 3: DFT-computed energy differences of the stereoisomers of 10a and 10h.
Scheme 3: Mechanistic rationale of the three-component sequence furnishing the 1-styryleth-2-enylideneindolon...
Figure 4: DFT-computed (B3LYP functional, 6-31G* basis set) HOMO (left) and LUMO (right) of merocyanine 8a.
Figure 5: Absorption and emission spectrum of the dropcasted film of compound 8a (recorded at room temperatur...
Figure 6: Absorption spectrum of the dropcasted film of compound 10d (recorded at room temperature, normalize...
Figure 7: Absorption spectra of compound 10h in dichloromethane (right trace) and of the dropcasted film (lef...
Figure 8: DFT-computed (B3LYP functional, 6-311G(d,p) basis set) FMOs (HOMO, bottom; LUMO (center), and LUMO+...
A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides
- Antoine Pignon,
- Erwan Le Gall and
- Thierry Martens
Beilstein J. Org. Chem. 2014, 10, 425–431, doi:10.3762/bjoc.10.39
Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea
- Jie-Ping Wan,
- Yunfang Lin,
- Kaikai Hu and
- Yunyun Liu
Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25
- selectively provide various 1,3-thiazine derivatives 4 [35]. Amazingly, a generally applicable alkyne-based method regioselectively yielding DHPMs has not yet been achieved [36]. Herein, we report the regioselective three-component synthesis of DHPMs employing alkynes, aldehydes and ureas/thioureas by making
- with an X-4A instrument without correcting the temperature, IR spectra were measured in KBr on a Spectrum One apparatus and the HRMS were obtained under ESI mode in a Bruker 7-tesla FT-ICR MS instrument. General procedure for the three-component synthesis of DHPMs 5 Aldehyde 1 (0.3 mmol), urea/thiourea
Graphical Abstract
Figure 1: Some DHPMs-based lead compounds.
Scheme 1: Regioselective 1,3-thiazines and DHPMs via aldehydes, ureas/thioureas and alkynes.
Scheme 2: Synthesis of enamino ester intermediate and its transformation to DHPM.
Scheme 3: Proposed reaction mechanism.
