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铜催化环丙基酮的扩环反应/N-酰基亚胺离子的形成/杂环-[4 + 2]-环加成反应：一条合成取代五环异吲哚啉-1-酮的途径

Copper-Catalyzed Ring Expansion of Cyclopropyl Ketones/Formation of N-acyliminium/Hetero-[4 + 2]-Cycloaddition: A Route to Substituted Pentacyclic Isoindolin-1-one.

作者信息

Li Jian, Bai Shuhua, Li Yang, Wang Zhengbing, Huo Xiaoyu, Liu Li

机构信息

School of Pharmaceutical Engineering & Life Sciences , Changzhou University , Changzhou , 213164 , China.

School of Petrochemical Engineering , Changzhou University , Changzhou , 213164 , China.

出版信息

J Org Chem. 2018 Aug 3;83(15):8780-8785. doi: 10.1021/acs.joc.8b01120. Epub 2018 Jul 3.

DOI:10.1021/acs.joc.8b01120
PMID:29920100
Abstract

A Cu-catalyzed three-component cascade cyclization among 2-formylbenzonitrile, cyclopropyl ketones, and diaryliodonium salts for the construction of fused isoindolin-1-one compounds is achieved. Pentacyclic isoindolinone derivatives could be obtained in moderate to good yields. The proposed mechanism involved a ring expansion of cyclopropyl ketones/formation of N-acyliminium/hetero-[4 + 2]-cycloaddition process.

摘要

实现了铜催化的2-甲酰基苯甲腈、环丙基酮和二芳基碘鎓盐之间的三组分串联环化反应，用于构建稠合异吲哚啉-1-酮化合物。可以以中等至良好的产率获得五环异吲哚啉酮衍生物。提出的机理涉及环丙基酮的扩环/N-酰基亚胺正离子的形成/杂环-[4+2]-环加成过程。

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