Rearrangement of quinoxalin-2-ones when exposed to enamines generated in situ from ketones and ammonium acetate: method for the synthesis of 1-(pyrrolyl)benzimidazolones

J Org Chem. 2015 Feb 6;80(3):1375-86. doi: 10.1021/jo502135d. Epub 2015 Jan 12.

Abstract

The reaction of 3-benzoylquinoxalin-2(1H)-ones with enamines (generated in situ from ammonium acetate and the corresponding methylaryl(hetaryl)ketones) proceeds smoothly to give the corresponding substituted 1-(pyrrolyl)benzimidazolone derivatives in moderate yields through the novel rearrangement of 3-benzoylquinoxalin-2(1H)-ones involving a dual cleavage of the C3═N4 and C2-C3 bonds under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Amines / chemistry*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry*
  • Catalysis
  • Ketones / chemistry*
  • Molecular Structure
  • Quinoxalines / chemistry*
  • Stereoisomerism

Substances

  • Acetates
  • Amines
  • Benzimidazoles
  • Ketones
  • Quinoxalines
  • benzimidazolone
  • ammonium acetate