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, cilt.20, sa.2, ss.139-145, 1996 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20 Sayı: 2
  • Basım Tarihi: 1996
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.139-145
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.