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

Demir A., Tanyeli C., Gulbeyaz V., Akgun H.

TURKISH JOURNAL OF CHEMISTRY, vol.20, no.2, pp.139-145, 1996 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 2
  • Publication Date: 1996
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), 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.