Synthesis of vertilecanin C and two new derivatives of vertilecanin A via nicotinic acid

DEMIRCI S., GÖKSU S., BOZTAS M., TUMER F., SEÇEN H.

TURKISH JOURNAL OF CHEMISTRY, cilt.32, sa.3, ss.287-295, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 32 Sayı: 3
  • Basım Tarihi: 2008
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.287-295
  • Anahtar Kelimeler: vertilecanin A, vertilecanin C, diarylketones, nicotinic acid, DOPAMINE BETA-HYDROXYLASE, PHENOPICOLINIC ACID
  • Atatürk Üniversitesi Adresli: Evet

Özet

Vertilecanin C and 2 new phenyl-substituted derivatives of vertilecanin A were synthesized. Lithiation of 5-benzoylpicolinamide with BuLi at -78 degrees C followed by treatment with methyl bromoacetate gave vertilecanin C [methyl 2-(3-benzoylpicolinamido) acetate], a natural product. Vertilecanin A type phenopicolinic acid derivatives were synthesized starting from nicotinic acid in 4 steps. Chlorination of nicotinic acid with SOCl(2) followed by treatment with anisole in the presence of AlCl(3) gave (4-methoxyphenyl)(pyridin-3-yl) methanone. The Minisci reaction of the ketone afforded 5-(4-methoxybenzoyl) picolinamide. TiCl(4)-catalyzed acidic hydrolysis of the picolinamide gave 5-(4-methoxybenzoyl) picolinic acid, from which 5-( hydroxy(4-methoxyphenyl) methyl) picolinic acid was obtained by selective reduction with NaBH(4). The same reaction sequence performed with toluene instead of anisole afforded 5-(hydroxy(p-tolyl) methyl) picolinic acid.