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碱介导的异吲哚酮的亚胺基酚和乙烯基酚与MBH碳酸酯的环化反应:直接合成二氢苯并呋喃和苯并呋喃衍生物。

Base-Mediated Annulation of -Iminophenols and -Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives.

作者信息

Wang Daqian, Liu Xing, Sun Jing, Han Ying, Yan Chao-Guo

机构信息

College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.

出版信息

J Org Chem. 2024 Nov 1;89(21):15472-15489. doi: 10.1021/acs.joc.4c01501. Epub 2024 Oct 15.

Abstract

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction -iminophenols and -vinylphenols with MBH carbonates of isatins under mild and metal-free conditions. The selective generation of different kinds of dihydrobenzofuran and benzofuran derivatives was successfully achieved by employing different substituted isatin-derived MBH carbonates with --tosyliminophenols and -vinylphenols. The features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, and atomic economy.

摘要

我们已经开发出一种简便的合成方法,通过路易斯碱介导的环化反应,在温和且无金属的条件下,由异吲哚酮的MBH碳酸酯与亚胺基苯酚和乙烯基苯酚高效构建重要的二氢苯并呋喃和苯并呋喃骨架。通过使用不同取代的异吲哚酮衍生的MBH碳酸酯与对甲苯磺酰亚胺基苯酚和乙烯基苯酚,成功实现了不同种类二氢苯并呋喃和苯并呋喃衍生物的选择性生成。其特点包括广泛的底物范围、优异的官能团兼容性、高分子多样性和原子经济性。

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