Synthesis of Fully Substituted 5-(o-Hydroxybenzoyl)imidazoles via Iodine-Promoted Domino Reaction of Aurones with Amidines

J Org Chem. 2022 Dec 16;87(24):16204-16212. doi: 10.1021/acs.joc.2c01680. Epub 2022 Nov 22.

Abstract

An iodine-promoted domino reaction of aurones with amidines has been successfully explored. The reaction proceeds in a consecutive manner containing Michael addition, iodination, cyclization from intramolecular nucleophilic substitution, and dehydrogenative aromatization from spiro ring opening. Following this novel strategy, a variety of 1,2,4-trisubstituted 5-(o-hydroxybenzoyl)imidazoles were efficiently synthesized in moderate to good yields from readily available starting materials. A plausible mechanism has been proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines*
  • Cyclization
  • Imidazoles
  • Iodine*

Substances

  • Amidines
  • Imidazoles
  • Iodine
  • aurone