Coumarin-3-carboxylic acid: C3/C4-functionalizations and cyclization reactions

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Fatemeh Doraghi, Mehdi Ghanbarlou, Amir Mohammad Mahdavian, Bahareh Bari, Bagher Larijani, Mohammad Mahdavi
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引用次数: 0

Abstract

Due to the presence of a carboxyl group, coumarin-3-carboxylic acid can easily participate in C3-, and C4-functionalization, as well as cyclization reactions. The carboxyl moiety as a directing group enhances the reactivity of coumarins as dienophiles, which facilitates the participation of these scaffolds in the synthesis of various heterocycles. Hence, this review highlights the reports since 2010 on the contribution of coumarin-3-carboxylic acids in decarboxylative and cyclization reactions and discusses interesting reaction mechanisms.

Graphical abstract

Coumarins are privileged O-heterocycles and appear in biologically active natural and medicinal products. The presence of carboxyl as a directing group allowed coumarin-3-carboxylic acid to participate in C3-, or C4-functionalization, and annulations. This compound has attracted extensive attention from chemists in the field of cross-coupling methodologies to provide functionalized structures.

Abstract Image

香豆素-3-羧酸:C3/C4 功能化和环化反应
摘要由于羧基的存在,香豆素-3-羧酸很容易参与 C3 和 C4 功能化以及环化反应。羧基作为定向基团提高了香豆素作为亲二烯化合物的反应活性,从而促进了这些支架参与各种杂环化合物的合成。因此,本综述重点介绍了 2010 年以来有关香豆素-3-羧酸在脱羧反应和环化反应中的贡献的报道,并讨论了有趣的反应机理。羧基作为定向基团的存在使香豆素-3-羧酸能够参与 C3 或 C4 功能化和环化反应。这种化合物吸引了交叉偶联方法领域化学家的广泛关注,以提供功能化结构。
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来源期刊
Journal of Chemical Sciences
Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.10
自引率
5.90%
发文量
107
审稿时长
1 months
期刊介绍: Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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