A palladium-catalyzed ring-expansion reaction of cyclobutanols with 2-haloanilines leading to benzazepines and quinolines

A general synthesis of 2-aryl benzazepines has been developed through palladium-catalyzed ring-expansion reactions of cyclobutanols with 2-haloanilines; the further oxidative rearrangement reaction of benzazepines provided an efficient synthesis of 2-acyl quinolines. These transformations feature th...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-10, Vol.57 (79), p.1234-1237
Main Authors: Shen, Xiao-Qin, Yan, Xiao-Wei, Zhang, Xing-Guo
Format: Article
Language:English
Subjects:
Chemical reactions
Functional groups
Organic compounds
Palladium
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Summary:A general synthesis of 2-aryl benzazepines has been developed through palladium-catalyzed ring-expansion reactions of cyclobutanols with 2-haloanilines; the further oxidative rearrangement reaction of benzazepines provided an efficient synthesis of 2-acyl quinolines. These transformations feature the efficient construction of six- and seven-membered N -containing heterocycles from easily obtained materials with excellent functional group tolerance. A palladium-catalyzed ring-expansion reaction of cyclobutanols for the synthesis of 2-aryl benzazepines has been developed, which could be further converted to 2-acyl quinolines through hydrolysis, amination and dehydrogenation processes.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc04395a