3-haloquinolines by Friedländer reaction of α-haloketones

J Org Chem. 2011 Jul 15;76(14):5774-81. doi: 10.1021/jo2008252. Epub 2011 Jun 15.

Abstract

A general approach to 3-fluoro-, 3-chloro-, and 3-bromoquinolines which relies on organosilane-promoted Friedländer reaction of α-haloketones is described. The scope of the methylene component as well as influence of the organosilane component on the outcome of the reaction is studied. The method can be used under parallel synthesis conditions.

MeSH terms

  • Ketones / chemistry*
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

  • Ketones
  • Quinolines