New fatty acid derivatives based on barbiturates and other cyclic beta-dicarbonyl compounds and an acyl migration

Pesyan N. N., Bagheri M., ŞAHİN E., TUNÇ T.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, cilt.11, sa.5, ss.1429-1437, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 5
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1007/s13738-014-0415-9
  • Dergi Adı: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1429-1437
  • Atatürk Üniversitesi Adresli: Evet

Özet

The use of DCC, triethylamine and 4-dimethylaminopyridine in dichloromethane provides a general and standard one-pot procedure for the O-acylation of cyclic beta-dicarbonyl compound derivatives (1) with palmitic and stearic acids which have long hydrocarbon tails, to synthesis of new type of fatty acid derivative in good to excellent yields. Structure elucidation was carried out by FT-IR, H-1 NMR and C-13 NMR spectroscopy techniques. The acyl migration was also found in results and the corresponding structure was characterized by X-ray crystallography. A proposed mechanism was discussed for the formation of products.