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Silver‐Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone‐Fused Carbo‐ and Heterocycles
Author(s) -
Hu Zhongyan,
Dong Jinhuan,
Men Yang,
Lin Zhichen,
Cai Jinxiong,
Xu Xianxiu
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611024
Subject(s) - annulation , catalysis , combinatorial chemistry , domino , chemistry , aryl , stereochemistry , organic chemistry , alkyl
A silver‐catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α‐substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2‐aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a 13 C‐labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α‐amidoketenimine intermediate, which undergoes 1,3‐amino migration to form an α‐imidoylketene, followed by 6 π electrocyclization.