Alkylidene oxindoles: A versatile building block towards formation of diverse organic frameworks

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-06-02 DOI:10.1016/j.tet.2025.134757

Sayan Pramanik , Rajiv Karmakar , Chhanda Mukhopadhyay

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引用次数: 0

Abstract

3-Alkylidene-2-oxindoles are highly reactive intermediates in several key organic reactions. In Michael addition, they readily react with nucleophiles to form carbon-carbon bonds. In multicomponent reactions, they enable the efficient assembly of complex polycyclic structures. Their involvement in cycloaddition reactions facilitates the formation of biologically active, fused ring systems. Enantioselective reactions with 3-alkylidene-2-oxindoles provide chiral molecules with high stereochemical control, crucial for drug development. Additionally, they participate in metal- and radical-mediated C–H functionalization, enabling direct modification of C–H bonds for efficient functionalization in complex molecule synthesis. In this review, we discuss about diverse reactions of 3-alkylidene-2-oxindoles (Mainly Michael addition, multicomponent domino reaction, cycloaddition reaction, enantioselective transformations, C–H functionalization reaction drived by transition metal and radical) that may provide as a section of consistent literature for further research.

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烷基二烯氧吲哚：形成多种有机框架的通用构建块

3-烷基烷-2-氧吲哚是几种关键有机反应的高活性中间体。此外，它们很容易与亲核试剂反应形成碳-碳键。在多组分反应中，它们可以有效地组装复杂的多环结构。它们参与环加成反应，促进了生物活性，融合环体系的形成。与3-烷基烯-2-氧吲哚的对映选择性反应提供了具有高度立体化学控制的手性分子，对药物开发至关重要。此外，它们还参与金属和自由基介导的C-H功能化，从而能够直接修饰C-H键，从而在复杂分子合成中实现高效功能化。本文综述了3-烷基烯-2-氧吲哚的各种反应（主要是Michael加成反应、多组分多米诺反应、环加成反应、对映选择性转化、过渡金属和自由基驱动的碳氢官能化反应），为进一步的研究提供了一致的文献。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.