Synthesis of functionalized coumarins and quinolinones by NHC-catalyzed annulation of modified enals with heterocyclic C-H acids

J Org Chem. 2014 May 2;79(9):4245-51. doi: 10.1021/jo500693h. Epub 2014 Apr 21.

Abstract

N-Heterocyclic carbene (NHC) catalyzed lactonization and lactamization of 2-bromoenals with heterocyclic C-H acids proceeding via the α,β-unsaturated acyl azolium intermediates is reported. The reaction furnished coumarin- or quinolinone-fused lactone/lactam derivatives. In addition, results of the enantioselective version of this reaction using chiral NHC are presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry

Substances

  • Acids
  • Coumarins
  • Heterocyclic Compounds
  • Quinolones
  • carbene
  • Methane