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Search for "isatoic anhydride" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects
- Shivani Gulati,
- Stephy Elza John and
- Nagula Shankaraiah
Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71
Graphical Abstract
Figure 1: Marketed drugs with acridine moiety.
Scheme 1: Synthesis of 4-arylacridinediones.
Scheme 2: Proposed mechanism for acridinedione synthesis.
Scheme 3: Synthesis of tetrahydrodibenzoacridinones.
Scheme 4: Synthesis of naphthoacridines.
Scheme 5: Plausible mechanism for naphthoacridines.
Figure 2: Benzoazepines based potent molecules.
Scheme 6: Synthesis of azepinone.
Scheme 7: Proposed mechanism for azepinone formation.
Scheme 8: Synthesis of benzoazulenen-1-one derivatives.
Scheme 9: Proposed mechanism for benzoazulene-1-one synthesis.
Figure 3: Indole-containing pharmacologically active molecules.
Scheme 10: Synthesis of functionalized indoles.
Scheme 11: Plausible mechanism for the synthesis of functionalized indoles.
Scheme 12: Synthesis of spirooxindoles.
Scheme 13: Synthesis of substituted spirooxindoles.
Scheme 14: Plausible mechanism for the synthesis of substituted spirooxindoles.
Scheme 15: Synthesis of pyrrolidinyl spirooxindoles.
Scheme 16: Proposed mechanism for pyrrolidinyl spirooxindoles.
Figure 4: Pyran-containing biologically active molecules.
Scheme 17: Synthesis of functionalized benzopyrans.
Scheme 18: Plausible mechanism for synthesis of benzopyran.
Scheme 19: Synthesis of indoline-spiro-fused pyran derivatives.
Scheme 20: Proposed mechanism for indoline-spiro-fused pyran.
Scheme 21: Synthesis of substituted naphthopyrans.
Figure 5: Marketed drugs with pyrrole ring.
Scheme 22: Synthesis of tetra-substituted pyrroles.
Scheme 23: Mechanism for silica-supported PPA-SiO2-catalyzed pyrrole synthesis.
Scheme 24: Synthesis of pyrrolo[1,10]-phenanthrolines.
Scheme 25: Proposed mechanism for pyrrolo[1,10]-phenanthrolines.
Figure 6: Marketed drugs and molecules containing pyrimidine and pyrimidinones skeletons.
Scheme 26: MWA-MCR pyrimidinone synthesis.
Scheme 27: Two proposed mechanisms for pyrimidinone synthesis.
Scheme 28: MWA multicomponent synthesis of dihydropyrimidinones.
Scheme 29: Proposed mechanism for dihydropyrimidinones.
Figure 7: Biologically active fused pyrimidines.
Scheme 30: MWA- MCR for the synthesis of pyrrolo[2,3-d]pyrimidines.
Scheme 31: Proposed mechanism for pyrrolo[2,3-d]pyrimidines.
Scheme 32: Synthesis of substituted pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 33: Probable pathway for pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 34: Synthesis of pyridopyrimidines.
Scheme 35: Plausible mechanism for the synthesis of pyridopyrimidines.
Scheme 36: Synthesis of dihydropyridopyrimidine and dihydropyrazolopyridine.
Scheme 37: Proposed mechanism for the formation of dihydropyridopyrimidine.
Scheme 38: Synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 39: Plausible mechanism for the synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 40: Synthesis of decorated imidazopyrimidines.
Scheme 41: Proposed mechanism for imidazopyrimidine synthesis.
Figure 8: Pharmacologically active molecules containing purine bases.
Scheme 42: Synthesis of aza-adenines.
Scheme 43: Synthesis of 5-aza-7-deazapurines.
Scheme 44: Proposed mechanism for deazapurines synthesis.
Figure 9: Biologically active molecules containing pyridine moiety.
Scheme 45: Synthesis of steroidal pyridines.
Scheme 46: Proposed mechanism for steroidal pyridine.
Scheme 47: Synthesis of N-alkylated 2-pyridones.
Scheme 48: Two possible mechanisms for pyridone synthesis.
Scheme 49: Synthesis of pyridone derivatives.
Scheme 50: Postulated mechanism for synthesis of pyridone.
Figure 10: Biologically active fused pyridines.
Scheme 51: Benzimidazole-imidazo[1,2-a]pyridines synthesis.
Scheme 52: Mechanism for the synthesis of benzimidazole-imidazo[1,2-a]pyridines.
Scheme 53: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanedione derivatives.
Scheme 54: Proposed mechanism for spiro-pyridines.
Scheme 55: Functionalized macrocyclane-fused pyrazolo[3,4-b]pyridine derivatives.
Scheme 56: Mechanism postulated for macrocyclane-fused pyrazolo[3,4-b]pyridine.
Scheme 57: Generation of pyrazolo[3,4-b]pyridines.
Scheme 58: Proposed mechanism for the synthesis of pyrazolo[3,4-b]pyridines.
Scheme 59: Proposed mechanism for the synthesis of azepinoindole.
Figure 11: Pharmaceutically important molecules with quinoline moiety.
Scheme 60: Povarov-mediated quinoline synthesis.
Scheme 61: Proposed mechanism for Povarov reaction.
Scheme 62: Synthesis of pyrazoloquinoline.
Scheme 63: Plausible mechanism for pyrazoloquinoline synthesis.
Figure 12: Quinazolinones as pharmacologically significant scaffolds.
Scheme 64: Four-component reaction for dihydroquinazolinone.
Scheme 65: Proposed mechanism for dihydroquinazolinones.
Scheme 66: Synthesis purine quinazolinone and PI3K-δ inhibitor.
Scheme 67: Synthesis of fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 68: Proposed mechanism for fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 69: On-water reaction for synthesis of thiazoloquinazolinone.
Scheme 70: Proposed mechanism for the thiazoloquinazolinone synthesis.
Scheme 71: β-Cyclodextrin-mediated synthesis of indoloquinazolinediones.
Scheme 72: Proposed mechanism for synthesis of indoloquinazolinediones.
Figure 13: Triazoles-containing marketted drugs and pharmacologically active molecules.
Scheme 73: Cu(I) DAPTA-catalyzed 1,2,3-triazole formation.
Scheme 74: Mechanism for Cu(I) DAPTA-catalyzed triazole formation.
Scheme 75: Synthesis of β-hydroxy-1,2,3-triazole.
Scheme 76: Proposed mechanism for synthesis of β-hydroxy-1,2,3-triazoles.
Scheme 77: Synthesis of bis-1,2,4-triazoles.
Scheme 78: Proposed mechanism for bis-1,2,4-triazoles synthesis.
Figure 14: Thiazole containing drugs.
Scheme 79: Synthesis of a substituted thiazole ring.
Scheme 80: Synthesis of pyrazolothiazoles.
Figure 15: Chromene containing drugs.
Scheme 81: Magnetic nanocatalyst-mediated aminochromene synthesis.
Scheme 82: Proposed mechanism for the synthesis of chromenes.
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
- ), and this was subsequently reacted with isatoic anhydride (IA) in EtOH under reflux conditions for 24 h. GO–CO–NH–IA was then reacted with copper iodide under reflux conditions to obtain GO–NH–IA–Cu(I) (88, Scheme 19). Gopidas et al. explored the catalytic activity of copper nanoparticles linked to
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.
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
- containing chlorine atoms in the portion coming from isatoic anhydride 56. In all cases, the most likely mechanism is initiated by a nucleophilic attack of amine 2 onto the anhydride carbonyl with opening of the cycle to form carbamic acid derivative 58 and loss of CO2 to give the intermediate 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.
Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives
- Nicholas G. Jentsch,
- Jared D. Hume,
- Emily B. Crull,
- Samer M. Beauti,
- Amy H. Pham,
- Julie A. Pigza,
- Jacques J. Kessl and
- Matthew G. Donahue
Beilstein J. Org. Chem. 2018, 14, 2529–2536, doi:10.3762/bjoc.14.229
- acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project. Keywords: cyclodehydration; HIV integrase; isatoic anhydride; masked acyl cyanide; quinoline; Introduction In stark contrast to the prevalence of the quinoline heterocycle in natural products [1
- regioselectivity issues and practical challenges associated with the aniline cyclocondensation (7→8), along with the scarcity of commercially available highly substituted quinolines, we sought to employ an entirely different tactic by utilizing 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride) chemistry [16][17
- gram of substrate) with subsequent stirring at room temperature for one hour. The isatoic anhydride products 9a–h typically precipitate out of solution and are readily collected by vacuum filtration. This reverse aqueous quench provides sufficiently pure material without the need for extraction with
Graphical Abstract
Figure 1: Investigational non-catalytic HIV-1 Integrase inhibitors.
Scheme 1: Boehringer Ingelheim retrosynthesis of quinoline 1.
Scheme 2: Quinoline ring condensation strategies.
Scheme 3: Isatoic anhydrides from anthranilic acids with triphosgene.
Scheme 4: Substituted 2-methyl-4-hydroxyquinolines from isatoic anhydrides and ethyl acetoacetate.
Scheme 5: Mechanistic hypothesis for the cyclocondensation reaction.
Scheme 6: Quinoline synthesis with ethyl acetylpyruvate.
Scheme 7: Elaboration of the benzoic acid ethyl ester to the acetic acid residue.
Scheme 8: Umpolung addition of ethoxycarbonyl via a MAC strategy.
Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups
- Nadia Gruber,
- Jimena E. Díaz and
- Liliana R. Orelli
Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227
- [40][62][63][64][65][66][67]. N-Arylations of this substrate have been attempted, although with poor results [68]. Alternative strategies leading to N-functionalized 2-ABAs start from isatoic anhydride, 2-nitrobenzonitrile, 2-nitrobenzaldehyde, 2-aminobenzophenone or 2-nitrobenzyl halides, among
Graphical Abstract
Figure 1: N-Aryl-3,4-dihydroquinazolines 1.
Scheme 1: Synthetic pathway leading to N-aryl-3,4-dihydroquinazolines 1.
Scheme 2: Synthesis of compounds 2.
Figure 2: Reaction intermediate in the synthesis of compound 2a.
Scheme 3: Addition–elimination mechanism for the heterocyclization.
Scheme 4: Proposed mechanism involving an intermediate nitrilium ion.
Experimental and theoretical investigations into the stability of cyclic aminals
- Edgar Sawatzky,
- Antonios Drakopoulos,
- Martin Rölz,
- Christoph Sotriffer,
- Bernd Engels and
- Michael Decker
Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221
- effects. Results and Discussion Synthesis of test compounds The synthesis of tetrahydroquinazolines substituted at the phenyl ring as well as at the 3-N nitrogen atom was achieved in 4 steps (Scheme 3). Briefly, isatoic anhydride was methylated using MeI to yield compound 4, followed by formation of
- reduction with LiAlH4. The introduction of different substitution patterns at the N-1 nitrogen atom was achieved using two pathways as shown in Scheme 4. Because the direct alkylation of isatoic anhydride in the first reaction step with different alkyl halides failed (Scheme 3), amide 10 was synthesized
- using isatoic anhydride and methylammonium hydrochloride (Scheme 4a) followed by cyclization under acidic conditions with benzaldehyde to yield dihydroquinazolinone 11. Unfortunately, the introduction of substituents at the N-1 in 11 with alkyl halides was only successful with n-PrBr in the presence of
Graphical Abstract
Figure 1: Compounds described in the literature containing an aminal core for various applications. The amina...
Scheme 1: Synthetic approaches for the formation of the tetrahydroquinazoline moiety. Dashed lines indicate b...
Scheme 2: Oxidation and reduction reactions of tetrahydroquinazolines. Dashed lines indicate both cyclized or...
Figure 2: Hydrolysis of the aminal core of tetrahydroquinazolines 1 into the corresponding diamines 2 and ald...
Scheme 3: Reagents and conditions: (i) MeI, DIPEA, DMAc, 40 °C, 24 h; (ii) R1-NH2 or MeNH3Cl and Et3N, DMF, 4...
Scheme 4: Reagents and conditions: (a) (i) MeNH3Cl, Et3N, DMF, 70 °C, 3 h; (ii) AcOH, 70 °C, 4 h; (iii) n-PrB...
Figure 3: pH-Stability test of the aminal core toward hydrolysis in dependency of different substitution patt...
Figure 4: Kinetic analysis of hydrolysis of reference compound 8a in dependency of different pH values and ca...
Figure 5: Differences in energy along the reaction coordinate using the functional B3LYP-D3 for the hydrolysi...
Figure 6: Reaction equilibrium between tetrahydroquinazoline 1, the corresponding diamine 2 and aldehyde 3 in...
Figure 7: Minimum energy conformers in their neutral form with (a) an axial orientation of the phenyl system ...
