Microwave-assisted combinatorial synthesis of polysubstituent imidazo[1,2-a]quinoline, pyrimido[1,2-a]quinoline and quinolino[1,2-a]quinazoline derivatives

J Comb Chem. 2007 Nov-Dec;9(6):1144-8. doi: 10.1021/cc700124g. Epub 2007 Oct 23.

Abstract

A series of unusual fused heterocyclic compound derivatives, consisting of a pyridine and a imidazole or pyrimidine core, with a bridgehead nitrogen, were successfully synthesized by a microwave-assisted, three-component domino reaction of aldehydes, enaminones, and malononnitrile. In this one-pot reaction, up to five new bonds were formed accompanied by generating the lactam group. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environment impact.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Combinatorial Chemistry Techniques*
  • Imidazoles / chemistry*
  • Microwaves*
  • Models, Chemical
  • Nitriles / chemistry
  • Nitrogen / chemistry
  • Pyrimidines / chemistry*
  • Quinazolines / chemical synthesis*
  • Quinolines / chemical synthesis*

Substances

  • Aldehydes
  • Imidazoles
  • Nitriles
  • Pyrimidines
  • Quinazolines
  • Quinolines
  • imidazole
  • quinoline
  • pyrimidine
  • Nitrogen