Three-component reaction of a 2-aminoazine, a 2-oxoaldehyde, and a cyclic 1,3-dicarbonyl compound for the synthesis of imidazo[1,2-a]azine derivatives

ACS Comb Sci. 2014 Oct 13;16(10):535-42. doi: 10.1021/co5000695. Epub 2014 Aug 29.

Abstract

A three-component reaction of a 2-aminoazine, a 2-oxoaldehyde, and a cyclic 1,3-dicarbonyl compound providing access toward a novel class of imidazo[1,2-a]azine derivatives was developed and studied. The scope of the process was thoroughly explored under three different reaction conditions resulting in the generation of a small library of title compounds and highlighting the possibility of case-specific approach.

Keywords: 1,3-dicarbonyl compounds; 2-aminoazines; 2-oxoaldehydes; imidazo[1,2-a]azines; multicomponent reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • GABA-A Receptor Agonists / chemical synthesis
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry*
  • Indicators and Reagents
  • Ketones / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Small Molecule Libraries

Substances

  • Aldehydes
  • GABA-A Receptor Agonists
  • Imidazoles
  • Indicators and Reagents
  • Ketones
  • Small Molecule Libraries