Enantioselective synthesis of 4-hydroxy-3-(3-oxo-l-phenyl butyl)-2H-1-benzopyran-2-one (Warfarin)

DEMİR A. G., TANYELİ C., Gülbeyaz V., Akgün H.

Turkish Journal of Chemistry, vol.20, no.2, pp.139-145, 1996 (Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 2
  • Publication Date: 1996
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.139-145
  • Middle East Technical University Affiliated: Yes

Abstract

Oral anticoagulant Warfarin (4-hydroxy-3-(3-oxo-1-phenyl butyl)-2H-1-benzopyran-2-one) is synthesized in optically active form starting from 4-hydroxycoumarin via formation of optically active enamines followed by Michael addition reaction with benzyliden acetone at low temperature. Different amines gave 17-68% ee and the chemical yield was 22-71%, depending on the reaction conditions and the structure of chiral amines.