TFA-mediated tandem Friedel-Crafts alkylation/cyclization/hydrogen transfer process for the synthesis of flavylium compounds

J Org Chem. 2007 Nov 23;72(24):9383-6. doi: 10.1021/jo7015604. Epub 2007 Nov 1.

Abstract

The tandem reaction of phenols and chalcones in refluxing TFA gave the flavylium species of 2-hydroxy-2-phenyl-2H-chromenes in moderate to good isolated yields. The reaction was proposed to involve a tandem transformation of Friedel-Crafts alkylation, dehydrative cyclization, intermolecular hydrogen transfer, and hydration. As a multifunctional catalyst, TFA mediated the processes efficiently and cleanly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Anthocyanins / chemical synthesis*
  • Cyclization
  • Flavonoids / chemical synthesis*
  • Hydrogen / chemistry*
  • Models, Chemical
  • Trifluoroacetic Acid / chemistry*

Substances

  • Anthocyanins
  • Flavonoids
  • Hydrogen
  • Trifluoroacetic Acid