Two efficient cascade reactions to synthesize substituted furocoumarins

J Org Chem. 2008 Jun 20;73(12):4732-5. doi: 10.1021/jo800439y. Epub 2008 May 28.

Abstract

We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H(2)O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4 H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl(2) as the oxidant afforded the 3-chloro-2-substituted-4 H-furo[3,2- c]chromen-4-one 3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chlorine / chemistry
  • Cyclization
  • Furocoumarins / chemical synthesis*
  • Furocoumarins / chemistry
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Furocoumarins
  • Chlorine