A one-step synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid esters from o-nitrobenzaldehydes

J Org Chem. 2010 May 21;75(10):3488-91. doi: 10.1021/jo100392x.

Abstract

A straightforward and efficient one-step procedure for the synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters is described. The simple reductive cyclization is carried out by treating various substituted o-nitrobenzaldehydes with inexpensive, commercially available 3,3-diethoxypropionic acid ethyl ester and SnCl(2).2H(2)O in refluxing ethanol.

MeSH terms

  • Benzaldehydes / chemistry*
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

  • Benzaldehydes
  • Carboxylic Acids
  • Esters
  • Quinolines
  • 2-nitrobenzaldehyde