{"title":"Decarboxylation and cross-coupling reactions of coumarin-3-carboxylic acid: A comprehensive review","authors":"","doi":"10.1016/j.tet.2024.134238","DOIUrl":null,"url":null,"abstract":"<div><p>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.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024004186","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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.
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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