Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: efficient synthesis of flavones under mild reaction conditions

Org Biomol Chem. 2011 Oct 21;9(20):6930-3. doi: 10.1039/c1ob06209c. Epub 2011 Sep 6.

Abstract

Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Flavones / chemical synthesis*
  • Iodides / chemistry*
  • Ionic Liquids / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Flavones
  • Iodides
  • Ionic Liquids
  • Copper
  • cuprous iodide