A new rapid multicomponent domino heteroannulation of heterocyclic ketene aminals: solvent-free regioselective synthesis of functionalized benzo[g]imidazo[1,2-a]quinolinediones

Org Biomol Chem. 2013 Feb 7;11(5):781-6. doi: 10.1039/c2ob27137k. Epub 2012 Dec 7.

Abstract

A highly efficient and straightforward three-component cascade reaction was developed to synthesize benzo[g]imidazo[1,2-a]quinolinedione derivatives from heterocyclic ketene aminals (HKAs), aldehydes, and 2-hydroxy-1,4-naphthoquinone (HNQ) via Et(3)N-catalyzed tandem [3 + 2 + 1] annulation under solvent-free conditions. The reactions were very mild, convenient and highly regioselective to form new fused tetracyclic target molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry
  • Amines / chemistry*
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Ethylenes / chemistry*
  • Ketones / chemistry*
  • Models, Molecular
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

  • Acetals
  • Amines
  • Benzene Derivatives
  • Ethylenes
  • Ketones
  • Quinolines
  • ketene