A multicomponent coupling sequence for direct access to substituted quinolines

Org Lett. 2009 Oct 15;11(20):4720-3. doi: 10.1021/ol901855b.

Abstract

A titanium-catalyzed three-component coupling reaction can be used to generate tautomers of N-aryl-1,3-diimines. Simple treatment of these products with acetic acid leads to cyclization forming quinoline derivatives in a one-pot procedure. The primary amines employed can be substituted anilines, aminonaphthalenes, or even heterocyclic amines, which leads to a variety of fused-ring heterocyclic frameworks. The one-pot yields varied from 25-71% for the 18 examples presented in this study.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetates / chemistry
  • Amines / chemistry
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*

Substances

  • Acetates
  • Amines
  • Quinolines