Base-Promoted Annulation of Amidoximes with Alkynes: Simple Access to 2,4-Disubstituted Imidazoles

Molecules. 2020 Aug 9;25(16):3621. doi: 10.3390/molecules25163621.

Abstract

An efficient construction of imidazole ring by a Cs2CO3-promoted annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synthetic route with high atom-utilization for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Internal alkynes can also undergo the annulation to give 2,4,5-trisubstituted imidazoles.

Keywords: 2,4-disubstituted imidazoles; alkynes; amidoximes; annulation; base-promoted.

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Imidazoles / chemical synthesis*
  • Molecular Structure
  • Oximes / chemistry*

Substances

  • Alkynes
  • Imidazoles
  • Oximes
  • amidoxime