Syntheses of 4-Indolylquinoline Derivatives via Reductive Cyclization of Indolylnitrochalcone Derivatives by Fe/HCl

Molecules. 2015 Dec 15;20(12):22499-519. doi: 10.3390/molecules201219862.

Abstract

An easy and efficient procedure for the synthesis of 4-indolylquinoline derivatives is described. This process involves two steps, the first of which is the Michael addition of indole to nitrochalcones promoted by sulfamic acid under solvent free conditions and the second step is a reductive cyclization of the indolylnitrochalcone intermediates to 4-indolylquinoline derivatives by Fe/HCl in ethanol. In both steps, the reactions are clean and the yields of products are high.

Keywords: 4-indolylquinoline; Fe/HCl; indolylchalcone; reductive cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chalcones / chemistry*
  • Chlorides / chemistry*
  • Cyclization
  • Ferric Compounds / chemistry*
  • Hydrochloric Acid / chemistry*
  • Indoles / chemical synthesis*
  • Oxidation-Reduction
  • Quinolines / chemical synthesis*
  • Sulfonic Acids / chemistry

Substances

  • Chalcones
  • Chlorides
  • Ferric Compounds
  • Indoles
  • Quinolines
  • Sulfonic Acids
  • sulfamic acid
  • Hydrochloric Acid
  • ferric chloride