FeCl3·6H2O-catalyzed intramolecular allylic amination: synthesis of substituted dihydroquinolines and quinolines

J Org Chem. 2012 Oct 5;77(19):8615-20. doi: 10.1021/jo301560w. Epub 2012 Sep 25.

Abstract

A facile and efficient method to synthesize 2- or 4-substituted 1,2-dihydroquinolines and quinolines catalyzed by FeCl(3)·6H(2)O (2 mol %) was described. The iron-catalyzed intramolecular allylic amination of 2-aminophenyl-1-en-3-ols proceeded smoothly to afford 13 1,2-dihydroquinoline and 8 quinoline derivatives under mild reaction conditions with good to excellent yields (up to 96%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Catalysis
  • Chlorides / chemistry*
  • Cyclization
  • Ferric Compounds / chemistry*
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Chlorides
  • Ferric Compounds
  • Quinolines
  • ferric chloride