Study of hydrolytic stability of glycolurils under alkaline conditions

Abstract

This article is devoted to the hydrolytic stability of glycoluryls, which are a promising class of organic compounds characterized by a wide spectrum of psychopharmacological activity. Hydrolysis of glycoluril and a mixture of N,N-dimethylglycoluryls was carried in alkaline conditions in water at reflux. The hydrolysis of a mixture of N,N-dimethylglycoluril was carried out for 5 days before the complete decomposition of the mixture of isomers. Quantitative and qualitative analysis of the hydrolyzates was carried out by high-performance liquid chromatography, thin layer chromatography, and gas chromatography / mass spectrometry. The mixture of N,N-dimethylglycoluril practically did not undergo hydrolysis during the first three days. The rate of hydrolysis of cis and trans isomers of N,N-dimethylglycoluril is the same. It means that the destruction of heterocycles occurs through the stages of successive hydrolytic cleavage of the C-N bond in the initial glycolyls and hydantoins: the glycolurils form anions which rearrange themselves into hydantoins by eliminating the corresponding ureas in alkaline conditions. The final products of hydrolysis of glycoluril and a mixture of the cis- and trans- isomers of N,N-dimethylglycoluril are hydantoic acids. The hydrolysis of glycoluril, as well as mixtures of the cis and trans isomers of N,N-dimethylglycoluril considered in the article can be used to evaluate hydrolytic stability, which in turn will give some information on the mechanisms of their action in the body.