Domino reaction to functionalized 2-hydroxybenzophenones from electron-deficient chromones and 1,3-dicarbonyl compounds

J Org Chem. 2011 Oct 21;76(20):8495-500. doi: 10.1021/jo201384f. Epub 2011 Sep 22.

Abstract

A base-promoted one-pot tandem reaction sequence has been developed to transform electron-deficient chromone-fused dienes 1 and 1,3-dicarbonyl compounds 2 to functionalized 2-hydroxybenzophenones 3 under mild conditions. This domino process, which involves multiple reactions, including Michael addition/cyclization/elimination, serves as an efficient, economic, and eco-friendly method for the construction of diversified 2-hydroxybenzophenone scaffolds without a transition-metal catalyst and inert atmosphere.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzophenones / analysis*
  • Benzophenones / chemical synthesis*
  • Carbonates / chemistry*
  • Catalysis
  • Chemistry, Pharmaceutical / methods*
  • Chromones / chemistry*
  • Cyclization
  • Electrons
  • Green Chemistry Technology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzophenones
  • Carbonates
  • Chromones
  • ortho-hydroxybenzophenone