Gold-catalyzed one-pot cascade construction of highly functionalized pyrrolo[1,2-a]quinolin-1(2H)-ones

J Org Chem. 2009 Oct 2;74(19):7344-8. doi: 10.1021/jo901418m.

Abstract

An efficient protocol was developed for the synthesis of fused heterocyclic multiring compounds pyrrolo[1,2-a]quinolin-1(2H)-ones via a AuBr(3)/AgSbF(6)-catalyzed cascade transformation. Significantly, the strategy affords a straightforward and efficient approach to construction of tricyclic lactam molecular architectures in which two new C-C bonds and one new C-N bond are formed in a one-pot synthetic operation from simple starting materials. Moreover, a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields and with excellent regio- and chemoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Gold Compounds / chemistry*
  • Molecular Structure
  • Organogold Compounds / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Stereoisomerism

Substances

  • Gold Compounds
  • Organogold Compounds
  • Pyrroles
  • Quinolones
  • pyrrolo(1,2-a)quinolin-1(2H)-one