A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes

Org Biomol Chem. 2007 Jan 7;5(1):61-4. doi: 10.1039/b613775j. Epub 2006 Nov 6.

Abstract

A highly effective one-pot Friedländer quinoline synthesis using inexpensive reagents has been developed. o-Nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of catalytic HCl (aq.) and subsequently condensed in situ with aldehydes or ketones to form mono- or di-substituted quinolines in high yields (66-100%).

MeSH terms

  • Aldehydes / chemistry*
  • Benzaldehydes / chemistry*
  • Iron / chemistry
  • Ketones / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Aldehydes
  • Benzaldehydes
  • Ketones
  • Quinolines
  • 2-nitrobenzaldehyde
  • Iron