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Search for "polysubstituted pyrroles" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.
Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives
- Yi Liu,
- Puying Luo,
- Yang Fu,
- Tianxin Hao,
- Xuan Liu,
- Qiuping Ding and
- Yiyuan Peng
Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163
- ]. Then, they also reported another CuH-catalyzed coupling reaction of 1,3-enynes 54 and nitrile to prepare polysubstituted pyrroles 55 (Scheme 21) [66]. The substrates 54 could be easily prepared by Sonogashira coupling of terminal alkynes and vinyl halides. It is worth mentioning that the addition of
Graphical Abstract
Scheme 1: Ag/I2-mediated electrophilic annulation of 2-en-4-ynyl azides 1.
Scheme 2: The proposed mechanism of Ag-catalyzed aza-annulation.
Scheme 3: The proposed mechanism of I2-mediated aza-annulation.
Scheme 4: Copper-catalyzed amination of (E)-2-en-4-ynyl azides 1.
Scheme 5: The proposed mechanism of copper-catalyzed amination.
Scheme 6: The derivatization of sulfonated aminonicotinates.
Scheme 7: Copper-catalyzed chalcogenoamination of (E)-2-en-4-ynyl azides 1.
Scheme 8: The possible mechanism of chalcogenoamination.
Scheme 9: The derivatization of 5‑selenyl- and 5-sulfenyl-substituted nicotinates.
Scheme 10: The tandem reaction of nitriles, Reformatsky reagents, and 1,3-enynes.
Scheme 11: Nickel-catalyzed [4 + 2]-cycloaddition of 3-azetidinones with 1,3-enynes.
Scheme 12: Electrophilic iodocyclization of 2-nitro-1,3-enynes to pyrroles.
Scheme 13: Electrophilic halogenation of 2-trifluoromethyl-1,3-enynes to pyrroles.
Scheme 14: Copper-catalyzed cascade cyclization of 2-nitro-1,3-enynes with amines.
Scheme 15: Tandem cyclization of 2-nitro-1,3-enynes, Togni reagent II, and amines.
Scheme 16: Tandem cyclization of 2-nitro-1,3-enynes, TMSN3, and amines.
Scheme 17: Cascade cyclization of 6-hydroxyhex-2-en-4-ynals to pyrroles.
Scheme 18: Au/Ag-catalyzed oxidative aza-annulation of 1,3-enynyl azides.
Scheme 19: The plausible mechanism of Au/Ag-catalyzed oxidative aza-annulation.
Scheme 20: Synthesis of 2-tetrazolyl-substituted 3-acylpyrroles from enynals.
Scheme 21: CuH-catalyzed coupling reaction of 1,3-enynes and nitriles to pyrroles.
Scheme 22: The mechanism of CuH-catalyzed coupling of 1,3-enynes and nitriles to pyrroles.
An efficient and facile access to highly functionalized pyrrole derivatives
- Meng Gao,
- Wenting Zhao,
- Hongyi Zhao,
- Ziyun Lin,
- Dongfeng Zhang and
- Haihong Huang
Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75
- complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of
- substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research. Keywords: azomethine ylides; 1,3-dipolar cycloaddition; one-pot synthesis; polysubstituted pyrroles; pyrrolo[3,4-c]pyrrole-1,3-diones
- considerable efforts have been expended to build stereogenic centers of pyrrolidine derivatives using chiral catalysts [7]. As our aim was to construct a small library of polysubstituted pyrroles for antibacterial screening, it prompted us to develop a concise and efficient synthesis of pyrrolo[3,4-c]pyrrole
Graphical Abstract
Figure 1: Representative pyrrolo[3,4-c]pyrrole-1,3-diones and polysubstituted pyrrole derivatives.
Scheme 1: Synthetic pathway for the preparation of pyrrolo[3,4-c]pyrrole-1,3-diones and highly substituted py...
Scheme 2: Scope of one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones 12a–k. General reaction conditions: ...
Scheme 3: Scope of the synthesis of highly substituted pyrrole derivatives 13a–n. General reaction conditions...
Scheme 4: Synthesis of 13k from 12d and ethylamine.
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
- 4:1 in the presence of 4 Å molecular sieves (Scheme 59) [97]. A sequential three-component enamine–azoene annulation reaction of primary aliphatic amines 292, activated methylene compounds 293, and 1,2-diaza-1,3-dienes (DDs, 294) has been reported to give polysubstituted pyrroles 295 (Scheme 60) [98
- . Multicomponent reaction of alkanedials, acetamide and acetyl chloride in the presence of PCl3 and acetic acid. An oxidative domino three-component synthesis of polyfunctionalized pyridines. A sequential one-pot three-component synthesis of polysubstituted pyrroles. Three-component decarboxylative coupling of
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.
