Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles

Jinxiong Cai; Haijie Bai; Yuan Wang; Xianxiu Xu; Haiming Xie; Jun Liu

doi:10.1039/c9cc01257e

Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles

Chem Commun (Camb). 2019 Mar 26;55(26):3821-3824. doi: 10.1039/c9cc01257e.

Authors

Jinxiong Cai¹, Haijie Bai, Yuan Wang, Xianxiu Xu, Haiming Xie, Jun Liu

Affiliation

¹ National & Local United Engineering Laboratory for Power Battery, Department of Chemistry, Northeast Normal University, Changchun, 130024, China. liuj975@nenu.edu.cn xiehm136@nenu.edu.cn.

PMID: 30869694
DOI: 10.1039/c9cc01257e

Abstract

A novel base-mediated regioselective [3+2] annulation of active methylene isocyanides with ketenimines has been developed. In the presence of t-BuOK, a wide range of ketenimines readily react with active methylene isocyanides in DMF at 40 °C to afford 1,4,5-trisubstituted imidazoles efficiently.