2H‐Azirines: Recent Progress in Synthesis and Applications

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(11)

Опубликована: Янв. 29, 2024

Abstract 2H ‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances the synthesis and functionalization of have been reported. Neber rearrangement, isomerization isoxazole, oxidation enamine, C−H bond activation, decomposition vinyl azide, alkyne, multi‐step developed for efficient assembly ‐azirines. As versatile highly strained unsaturated heterocycles, ‐azirines can be used as distinctive building blocks towards significant functional groups, attracted extensive attention fabrication numerous heterocycles. Recent studies focused on [3+n] ring‐expansion reactions, nucleophilic addition C=N double or continuous followed by cyclization, ring‐opening to acyclic compounds, substitution sp 3 ‐C−H One most critical challenges is seeking a selective opening specific three bonds azirine circle, some what achieved basis metal catalyst, photocatalysis, combination catalyst photocatalysis. In this review, recent involving reactivity accompanied with breakthroughs summarized. The review mainly covers period from 2019 2023.

Язык: Английский

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Direct Functionalization of para‐Quinones: A Historical Review and New Perspectives

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Май 21, 2024

Abstract The direct functionalization of quinones has always fascinated research communities due to their biological and redox activities subsequent application. Quinone motifs play a vital role as precursors for many bioactive compounds materials; hence, ingenious methodologies have been elaborated exploring these units. A significant part the synthetic strategies towards functionalized achieved by installing substituents on hydroquinones, phenols, or quinone itself different oxidative coupling reactions via radical pathways with without utilization metal catalysts. simple C−H bond remains challenging inherited electronic nature high dissociation energy. This review article summarizes recent advancement made through quinones. Our primary focus will be approaches mechanistic that appeared in last two decades, along short historical importance family.

Язык: Английский

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Recent advances on naphthoquinone-imidazolyl and naphthoquinone-thiazolyl derivatives as photoinitiators of photopolymerization

European Polymer Journal, Год журнала: 2024, Номер 219, С. 113401 - 113401

Опубликована: Авг. 27, 2024

Язык: Английский

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Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

New Journal of Chemistry, Год журнала: 2024, Номер 48(18), С. 8243 - 8276

Опубликована: Янв. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Язык: Английский

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High-yielding regioselective synthesis of p-quinone fused 5-substituted-1,4-benzodiazepine scaffolds via Pictet–Spengler type cycloannulation

New Journal of Chemistry, Год журнала: 2024, Номер 48(22), С. 10045 - 10052

Опубликована: Янв. 1, 2024

We designed a robust protocol to access p -quinone fused 5-substituted-1,4-benzodiazepine scaffolds, new molecular hybrid, through InCl 3 mediated Pictet–Spengler type cycloannulation of 2-amino-3-arylamino- and aldehydes.

Язык: Английский

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Reaction Course Dependent Regiospecific Transformation of 4‐Azido‐Coumarin into Coumarin C3‐C4 Fused Imidazole and 5‐Substituted‐1,4‐Benzodiazepine Scaffolds

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Июнь 19, 2024

Abstract Herein, we report an efficient route for coumarin C3‐C4 fused imidazole scaffolds via indium chloride‐mediated single‐step transformation of 4‐azido‐coumarin with amines/aldehydes and 5‐substituted‐1,4‐benzodiazepine 1,2‐azide‐nitrogen migration through two‐step sequential synthesis the transitory intermediacy 2,3‐bridged‐2 H ‐azirine. A plausible mechanistic pathway has been proposed from control/entrapment experiments 1 H‐NMR studies. This protocol provides reaction condition‐dependent product selectivity, structural diversification, excellent yields.

Язык: Английский

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Synthesis and biological evaluation of novel isoxazoloquinone derivatives as potent STAT3-targeting antipsoriasis agents

Bioorganic Chemistry, Год журнала: 2024, Номер 151, С. 107617 - 107617

Опубликована: Июль 9, 2024

Язык: Английский

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