Au(I)/Ag(I)-catalyzed cascade approach for the synthesis of benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinones

J Org Chem. 2013 May 3;78(9):4312-8. doi: 10.1021/jo400228g. Epub 2013 Apr 19.

Abstract

An efficient and facile Au(I)/Ag(I)-catalyzed cascade method has been developed for one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives through treatment of the substituted 2-(1H-benzo[d]imidazol-2-yl)anilines with 4-pentynoic acid or 5-hexynoic acid. The strategy features a Au(I)/Ag(I)-catalyzed one-pot cascade process involving the formation of three new C-N bonds in high yields, and with broad a substrate scope.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Gold / chemistry*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Silver / chemistry*

Substances

  • Imidazoles
  • Organometallic Compounds
  • Pyrroles
  • Quinazolinones
  • Silver
  • Gold