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路易斯酸催化双环丁烷与喹喔啉-2(1)-酮的形式[2π+2σ]环加成反应:合成喹喔啉稠合氮杂双环[2.1.1]己烷

Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1)-ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes.

作者信息

Zhang Kuan, Tian Shanghui, Li Wenke, Yang Xu, Duan Xin-Hua, Guo Li-Na, Li Pengfei

机构信息

Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage, Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.

School of Electrical Engineering, Xi'an Jiaotong University, Xi'an 710049, China.

出版信息

Org Lett. 2024 Jul 5;26(26):5482-5487. doi: 10.1021/acs.orglett.4c01775. Epub 2024 Jun 24.

Abstract

An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition of bicyclo[1.1.0]butanes and quinoxalin-2(1)-ones, facilitated by Lewis acid catalysis, is presented. This reaction is carried out under mild conditions and exhibits a broad substrate scope and excellent functional group tolerance.

摘要

本文报道了一种通过双环[1.1.0]丁烷与喹喔啉-2(1)-酮的分子间[2π+2σ]环加成反应,在路易斯酸催化下高效合成含有多个季碳中心的喹喔啉稠合氮杂双环[2.1.1]己烷的方法。该反应在温和条件下进行,具有广泛的底物范围和出色的官能团耐受性。

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