Decarboxylation and cross-coupling reactions of coumarin-3-carboxylic acid: A comprehensive review

IF 2.2 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-09-01 DOI:10.1016/j.tet.2024.134238
Seyyed Emad Hooshmand , Seyed Iman Alavioon , Maryam Saeb , Goutam Brahmachari , Morteza Shiri
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Abstract

The present review article offers an overview of the application of coumarin-3-carboxylic acids as a promising synthon in the synthesizing a diverse array of interesting biologically relevant organic molecules. This is accomplished, primarily through cross-coupling reactions, followed by subsequent decarboxylation, resulting in new reactivity patterns. The ability of the carboxylic acid moiety to enhance the electrophilic character of the directly attached olefinic carbon within a coumarin moiety, along with its feasibility for decarboxylation, opens up straightforward synthetic routes for numerous coumarin-derived molecules, including fused and hybrid heterocycles with remarkable regioselectivity (3-addition, 4-addition, or both). These advancements are primarily based on cascade reactions. This review article aims to provide readers with an up-to-date overview, encompassing contributions predominantly made in this challenging domain of organic synthesis during the last decade.

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香豆素-3-羧酸的脱羧和交叉偶联反应:全面综述
本综述文章概述了香豆素-3-羧酸作为一种有前途的合成物在合成各种有趣的生物相关有机分子中的应用。这主要是通过交叉偶联反应实现的,随后进行脱羧反应,从而产生新的反应模式。羧酸分子能够增强香豆素分子中直接连接的烯烃碳的亲电性,同时还具有脱羧的可行性,这为众多香豆素衍生分子开辟了直接的合成路线,包括具有显著区域选择性(3-加成、4-加成或两者兼有)的融合杂环。这些进展主要基于级联反应。这篇综述文章旨在为读者提供最新的综述,涵盖过去十年中在这一具有挑战性的有机合成领域的主要贡献。
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来源期刊
Tetrahedron
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.
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