Phosphorylation of glycoluryl derivatives with phosphorus pentachloride

Abstract

The paper presents the research results on the synthesis and study of new organophosphorus derivatives of glycoluril, obtained on the basis of pentavalent phosphorus. New organoelement phosphorus derivatives synthesized on the basis of N-acyl-substituted glycoluril have been obtained. They are of considerable interest due to the presence of effective reaction centers. Tetraacetyl-substituted glycoluril — 2,4,6,8-tetraacetyl- 2,4,6,8-tetraazabicyclo[3,3,0]octane-3,7-dione was chosen as the initial synthon. The use of unsubstituted glycoluril in the reaction of direct phosphorylation by the action of phosphorus trichloride or pentachloride is not possible due to the absence of active phosphorylation centers. It was experimentally shown that the reaction proceeds with prolonged heating for at least 48 hours in an argon. The initial acyl derivative of glycoluril and phosphorus pentachloride in the ratio of 1:6 and leads to the formation of diphosphonic complex of tetraacetylglycoluril — dihexachlorophosphorate 2,6-diacetyl-(4,8-diacetyl-2,4,6,8-tetraazabicyclo[ 3.3.0]octane-3,7-dione)-2,6-di(chloroethenyltrichlorophosphonium). The obtained compound is a white crystalline substance unstable in air. Decomposition of the diphosphonic complex was carried out using benzaldehyde and proceeds with the formation of the corresponding dichlorophosphate derivative, also unstable in air and rapidly decomposing at room temperature.