Study of hydrolytic stability of glycolurils under alkaline conditions

Kushcherbaeva, А. А. Бакибаев, D. A. Kurgachev, Fomchenkov, Zhaksybaeva, Malkov

2018

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DOI 10.31489/2018ch3/46-50
Data confidence 70 medium
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Abstract

Study of hydrolytic stability of glycolurils under alkaline conditionsThis 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.