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Communication | Special issue | Vol 52, No. 3, 2000, pp.1057-1064
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S130
Reactivity of Conjugated Phosphazenes Derived from Dehydroaspartic Esters with Acyl Halides. Synthesis of 5(4H)-Oxazolone

Francisco Palacios,* Marta Legido, Itziar Perez de Heredia, and Gloria Rubiales

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain

Abstract

The reactivity of N-vinylic phosphazenes derived from dehydroaspartic esters towards acyl halides is reported. Treatment of conjugated phosphazene with acyl halides led to the formation of N-acylated dehydroaspartic esters and alkenyl-5(4H) oxazolones. When the reaction was performed in the presence of diethylamine, 1-diethylamino-3,4-diethoxycarbonyl-2-aza-1,3-butadiene was obtained. Reaction of substituted 5(4H)-oxazolones with water, ethanol and amines gave N-acylated dehydroaspartic derivatives.