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

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 mechanis...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-08, Vol.83 (15), p.8780-8785
Main Authors: Li, Jian, Bai, Shuhua, Li, Yang, Wang, Zhengbing, Huo, Xiaoyu, Liu, Li
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01120