Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy

A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, a plausible mechanism for this reaction was...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-10, Vol.366 (19), p.4139-4144
Main Authors: Fu, Leiqing, Huang, Hongxiang, Jiang, Yingying, Liu, Xuan, Chen, Huimin, Wan, Jie‐Ping
Format: Article
Language:English
Subjects:
Chemical reactions
Chemical synthesis
Copper
C−H bond activation
Deuterium
Enaminone
Maleimide
Organic chemistry
Pyrrolo[3,4-e]isoindoles
Traceless directing group
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Summary:A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, a plausible mechanism for this reaction was proposed based on several control experiments, deuterium exchange experiments, and previous reports.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400509