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

Abstract

The use of DCC, triethylamine and 4-dimethylaminopyridine in dichloromethane provides a general and standard one-pot procedure for the O-acylation of cyclic β-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, 1H NMR and 13C 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.