New phosphorylated glycoluril derivatives

Abstract

The N-acylation of glycoluril with 1-haloacetyl halides was studied. The optimal conditions and reaction regioselectivity, as well as the effect of reagent molar ratios, base nature, temperature, and reaction time on the yield of the target product were established. It was shown that the chemical modification of the synthesized bis(bromoacetyl) derivative of glycoluril by phosphorylation by the classical Arbuzov reaction gave a previously unknown bis(diethylphosphonoacetyl) derivative of glycoluril. The consecutive silylation and hydrolysis of the latter derivative gave the corresponding bis(phosphonoacetyl) derivative which presents interest as a potentially biologically active compound.