Catalytic divergent synthesis of imidazoles via reaction condition-dependent [3 + 2] cyclization of TosMIC

A base-catalyzed divergent synthesis of multisubstituted imidazoles through TosMIC-based [3 + 2] cyclization reaction has been developed. In the presence of ketenimines and BuONa, 1,4,5-trisubstituted imidazoles were obtained. Nonetheless, in the absence of ketenimines, 1,4-disubstituted imidazole w...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-11, Vol.20 (44), p.8623-8627
Main Authors: Zhao, Cheng, Gu, Man-Zhen, Chen, Yi-Yuan, Hu, Xiao-Wei, Xu, Yi-Bing, Lin, Xiao-Min, Liu, Xin-Ni, Chen, Long, Chen, Guo-Shu, Liu, Yun-Lin
Format: Article
Language:English
Subjects:
Catalysis
Chemical synthesis
Cyanides
Cyclization
Imidazole
Imidazoles
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Summary:A base-catalyzed divergent synthesis of multisubstituted imidazoles through TosMIC-based [3 + 2] cyclization reaction has been developed. In the presence of ketenimines and BuONa, 1,4,5-trisubstituted imidazoles were obtained. Nonetheless, in the absence of ketenimines, 1,4-disubstituted imidazole was produced through cyclodimerization of TosMIC.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01747d