Synthesis of 2,3-dihydroquinolin-4(1H)-ones through catalytic metathesis of o-alkynylanilines and aldehydes

J Org Chem. 2009 Aug 7;74(15):5644-7. doi: 10.1021/jo900857c.

Abstract

SbF5-MeOH catalytic system efficiently promotes the alkyne-carbonyl metathesis of o-alkynylaniline derivatives and aldehydes to afford 2,3-disubstituted dihydroquinolinones in moderate to high yields with high trans-selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkynes / chemistry*
  • Aniline Compounds / chemistry*
  • Antimony / chemistry*
  • Catalysis
  • Fluorides / chemistry*
  • Methanol / chemistry*
  • Molecular Structure
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Stereoisomerism

Substances

  • 2,3-dihydroquinolin-4(1H)-one
  • Aldehydes
  • Alkynes
  • Aniline Compounds
  • Quinolones
  • antimony pentafluoride
  • Antimony
  • Fluorides
  • Methanol