Details

Autor(en) / Beteiligte

• GÖKSU, Süleyman
• TÜMER, Ferhan
• SEÇEN, Hasan
• DEMİRCİ, Serpil
• BOZTAŞ, Murat

Titel

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

Ist Teil von

• Turkish journal of chemistry, 2008-01, Vol.32 (3), p.287-295

Ort / Verlag

TÜBİTAK

Erscheinungsjahr

2008

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• Vertilecanin C and 2 new phenyl-substituted derivatives of vertilecanin A were synthesized. Lithi-ation of 5-benzoylpicolinamide with BuLi at -78 °C followed by treatment with methyl bromoac-etate 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. Chlo-rination of nicotinic acid with SOCl2 followed by treatment with anisole in the presence of AlCl3 gave (4-methoxyphenyl)(pyridin-3-yl)methanone. The Minisci reaction of the ketone afforded 5-(4-methoxybenzoyl)picolinamide. TiCl4-catalyzed acidic hydrolysis of the picolinamide gave 5-(4-methoxy-benzoyl)picolinic acid, from which 5-(hydroxy(4-methoxyphenyl)methyl)picolinic acid was obtained by selective reduction with NaBH4. The same reaction sequence performed with toluene instead of anisole afforded 5-(hydroxy(p-tolyl)methyl)picolinic acid.