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Cross‐Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]‐Cyclization of 1,4‐Diazabutatriene
Author(s) -
Hu Zhongyan,
Yuan Haiyan,
Men Yang,
Liu Qun,
Zhang Jingping,
Xu Xianxiu
Publication year - 2016
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.201600257
Subject(s) - cycloaddition , intramolecular force , chemistry , domino , combinatorial chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis
A new cross‐cycloaddition reaction between a wide range of isocyanides and 2‐isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4‐b]indoles under thermal conditions. On the basis of the experimental results and DFT calculations, a mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides to form 1,4‐diazabutatriene intermediates, followed by an intramolecular [3+2]‐cycloaddition and 1,3‐proton shift.