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Copper‐Catalyzed Three‐Component Synthesis of 2‐Iminodihydrocoumarins and 2‐Iminocoumarins
Author(s) -
Shen Yang,
Cui Sunliang,
Wang Jing,
Chen Xiaopeng,
Lu Ping,
Wang Yanguang
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900890
Subject(s) - chemistry , sulfonyl , piperidine , intramolecular force , catalysis , copper , michael reaction , nucleophile , combinatorial chemistry , nucleophilic addition , organic chemistry , medicinal chemistry , alkyl
An efficient synthesis of N ‐sulfonyl‐substituted 2‐imino‐3,4‐dihydrocoumarins and 2‐iminocoumarins via a copper‐catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and β‐( ortho ‐hydroxyphenyl)‐α,β‐unsaturated ketones or ortho ‐hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.