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模块化合成呋喃并[3,2-]色原酮-4-酮:Yb(OTf)催化4-羟基香豆素与β-硝基烯烃的[3 + 2]环化反应

Modular access to furo[3,2-]chromen-4-ones Yb(OTf)-catalyzed [3 + 2] annulation of 4-hydroxycoumarins with β-nitroalkenes.

作者信息

Wang Hua, Ma Qin, Xu Yifei, Sun Yanyan, Zhao Siyuan, Wang Shaoyin, He Xinwei

机构信息

Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University Wuhu 241002 P.R. China

Department of Chemistry, Wannan Medical College Wuhu 241002 China

出版信息

RSC Adv. 2024 Jun 18;14(27):19581-19585. doi: 10.1039/d4ra03962a. eCollection 2024 Jun 12.

Abstract

A facile and efficient strategy for modular access to furo[3,2-]chromen-4-ones using 4-hydroxycoumarin and β-nitroalkenes Lewis acid-catalyzed formal [3 + 2] annulation protocol is described. This reaction proceeds cascade Michael addition/nucleophilic addition/elimination in the presence of Yb(OTf), which involves the formation of two new σ (C-C and C-O) bonds for the construction of a novel furan ring in a single operation. This protocol affords a variety of functional groups, thereby providing a practical and efficient method for the fabrication of a furo[3,2-]chromen-4-one framework.

摘要

描述了一种使用4-羟基香豆素和β-硝基烯烃通过路易斯酸催化的形式[3 + 2]环化反应简便高效地模块化合成呋喃并[3,2 - ]色原酮-4-酮的策略。该反应在Yb(OTf)₃存在下通过串联迈克尔加成/亲核加成/消除进行,在一次操作中涉及形成两个新的σ(C-C和C-O)键以构建一个新的呋喃环。该方法提供了多种官能团,从而为构建呋喃并[3,2 - ]色原酮-4-酮骨架提供了一种实用高效的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6463/11184582/bdb5e728124d/d4ra03962a-f1.jpg

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