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

Org Biomol Chem. 2022 Nov 16;20(44):8623-8627. doi: 10.1039/d2ob01747d.

Abstract

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

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyanides*
  • Cyclization
  • Imidazoles*

Substances

  • Imidazoles
  • tosylmethyl isocyanide
  • Cyanides