Comprehensive Review of Dihydro‐2H‐pyrrol‐2‐one Derivatives

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract Heterocyclic chemistry has emerged as a significant field with diverse applications in recent scenarios. Nitrogen‐containing heterocyclic compounds have garnered attention due to their unique physiological characteristics and extensive medicinal utility. Therefore, the dihydro‐2 H ‐pyrrol‐2‐one scaffold is key skeleton for pharmaceutical research its high bioavailability wider synthetic applications. This study found that 1,5‐dihydro‐2 scaffolds can be used many ways. Thus, these been subject of lot years, but preparation main core harder because structure. covers methods over past 15 years synthesize substituted derivatives through variety reaction approaches by utilizing hybrid catalyzing systems, including photocatalysis, electrocatalysis, alkaline catalysts, acid organocatalysts, ionic liquid nanocatalysts, heterogeneous or homogeneous transitional‐metal catalysis (including Cu, Pd, Ni, Ru, Co, Fe, Si, Pt, Zn, etc.), well mechanism. review will encourage researchers exploit catalytic synthesis target compounds.

Language: Английский

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Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with ortho-Trifluoroacetyl Anilines under Redox-Neutral Conditions

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 5804 - 5816

Published: April 27, 2022

An efficient Cu-catalyzed annulation reaction of ketone oxime acetates with ortho-trifluoroacetyl anilines has been disclosed. With the developed protocol, a series 4-trifluoromethyl quinolines were obtained in good to excellent yields (58-99%) under redox-neutral conditions. The protocol also could be extended ferrocene-based for construction ferrocene-substituted fluorine-containing quinolines.

Language: Английский

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Cu‐Catalyzed Cascade Cyclization of Ketoxime Acetates and Alkynals Enabling Synthesis of Acylpyrroles

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(5), P. 1175 - 1180

Published: Jan. 23, 2021

Main observation and conclusion A facile copper‐based catalytic system has been developed to enable efficient cyclization of methylketoximes alkynals. This protocol provides a viable entry synthetically pharmaceutically useful 2‐acylpyrroles with broad range compatible functionalities. Mechanistically, key acyl migration is probably involved that leads the formation N ‐acyl pyrroles or otherwise NH by further hydrolysis. More importantly, present reaction also gives an opportunity realize three‐component pyrrole assembly simple addition carboxylic acid.

Language: Английский

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Copper-Catalyzed Bisannulations of Malonate-Tethered O-Acyl Oximes with Pyridine, Pyrazine, Pyridazine, and Quinoline Derivatives for the Construction of Dihydroindolizine-Fused Pyrrolidinones and Analogues

Organic Letters, Journal Year: 2021, Volume and Issue: 23(22), P. 8699 - 8704

Published: Nov. 1, 2021

A copper-catalyzed bisannulation reaction of malonate-tethered O-acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis structurally novel dihydroindolizine-fused pyrrolidinones their analogues. The present shows excellent regioselectivity stereoselectivity. Theoretical calculations reveal that coordination effect carbonyl group in nucleophilic substrate determines regioselectivity. Further functionalization generated pyrrolidinone could be easily realized through substitution, Michael addition, selective aminolysis, hydrolysis reactions.

Language: Английский

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Switchable assembly of substituted pyrimidines and 2H-imidazoles via Cu(i)-catalysed ring expansion of 2 methoxyl-2H-azirines

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(11), P. 3006 - 3011

Published: Jan. 1, 2022

The unprecedented switchable synthesis of substituted pyrimidines and 2 H -imidazoles via the Cu( i )-catalyzed ring expansion 2-methoxyl-2 -azirines is described.

Language: Английский

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Copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates for the synthesis of 3-aryl-4-pyrrolin-2-ones

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(35), P. 5225 - 5228

Published: Jan. 1, 2023

A copper-catalyzed [3+2] annulation of O -acyl ketoximes with 2-aryl malonates for the concise synthesis 3-aryl-4-pyrrolin-2-ones has been developed.

Language: Английский

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Asmic Isocyanide [3 + 2] Cascade to Dihydrooxazoles and Dihydroimidazoles

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(14), P. 9153 - 9160

Published: July 8, 2020

The versatile isocyanide building block Asmic, anisylsulfanylmethylisocyanide, reacts with aldehydes and ketones in a BF3·OEt2-mediated condensation to afford thioimidoyl-substituted 2,5-dihydrooxazoles. is distinguished from related base transition-metal-catalyzed [3 + 2] processes proceeding via the of 2 equiv an followed by molecular rearrangement that installs four new bonds. BF3·OEt2 mediates analogous Asmic imines generate N-substituted dihydroimidazoles. Mechanistically, activates facilitate deprotonation evolving zwitterion traps π-electrophiles formal process. A second deprotonation-condensation initiates structural involving sulfanyl elimination-addition transposition sequence. resulting dihydrooxazoles dihydroimidazoles contain thioimidate serves as diversification point for further elaboration.

Language: Английский

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Progress in Construction of 2H-Pyrrol-2-ones Skeleton

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(1), P. 57 - 57

Published: Jan. 1, 2023

Language: Английский

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Azide–Enolate Cycloaddition‐Rearrangement Enables Direct α‐Amination of Amides and Enelactam Synthesis from Esters**

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(31)

Published: Feb. 28, 2023

Azide-enolate cycloaddition-rearrangements offer potential for rapid access to diverse molecular frameworks from simple precursors. We report here that investigations into the cycloadditions of ester or amide enolates with vinyl azides led identification two reaction processes - direct α-amination amides and lactams, synthesis ene-γ-lactams esters. The outcomes these reactions depended on fate key triazoline intermediates generated in initial cycloaddition step. Isolation ene-γ-lactam revealed unexpected addition enolate equivalents, one which is later eliminated. Computational studies further suggested an unusual pathway involving terminal carbon N-vinyl triazoline. In contrast, lactams proceeded by rearrangement intermediate give imine, hydrolysis reduction gave primary secondary α-amino lactams.

Language: Английский

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I₂‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(37)

Published: July 19, 2023

Abstract A novel I 2 ‐DMSO‐mediated cascade cyclization approach for synthesizing 2‐hydroxy‐pyrrol‐3(2 H )‐one scaffold from readily accessible β ‐ketosulfoxonium ylides and ‐enaminone derivatives has been developed. Under metal‐free mild conditions, this transformation facilitates the formation of one C−C bond C−N in a single reaction vessel, exhibiting wide range functional group compatibility. In addition, method added an active hydroxyl to quaternary carbon center.

Language: Английский

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