Synthesis of Indole‐ and Pyrrole‐Fused Seven‐Membered Nitrogen Heterocycles via Acid‐Base Switchable Cyclization Involving Cleavage of Amide C−N Bonds

We report the method for synthesis of indole‐ and pyrrole‐fused seven‐membered nitrogen heterocycles by means of acid‐base switchable cyclization reactions. The reactions involved cleavage of amide C−N bonds, chemoselective N‐1 or C‐3 acylation, and 1,4‐Michael addition. This method could be used to...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-01, Vol.364 (2), p.281-285
Main Authors: Hao, Yanke, Zhou, Pan, Niu, Kaikai, Song, Hongjian, Liu, Yuxiu, Zhang, Jingjing, Wang, Qingmin
Format: Article
Language:English
Subjects:
Acylation
Chemical reactions
Chemoselective
Cleavage
Cyclization
C−N Bonds Cleavage
Nitrogen
Nitrogen Heterocycles
Switchable
Synthesis
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Summary:We report the method for synthesis of indole‐ and pyrrole‐fused seven‐membered nitrogen heterocycles by means of acid‐base switchable cyclization reactions. The reactions involved cleavage of amide C−N bonds, chemoselective N‐1 or C‐3 acylation, and 1,4‐Michael addition. This method could be used to construct two different kinds of seven‐membered rings in one step from the same starting material without the need for a transition‐metal catalyst.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101126