Study of uric acid oxidation reaction products in medium of ammonia or primary amines

Abstract

This work is considered in more detail the most important stage of obtaining one of the promising heteroatomic polycyclic compounds 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP). THAP is a potential compound for creating high-energy substances due to the presence of six nitrogen atoms in the structure and tight packing. Uric acid is the starting compound in the THAP synthesis chain. When it is oxidized by sodium persulfate or potassium ferrocyanide, 1,5-diaminoglycoluril is formed, from which the propellane structure is formed by the tricyclization reaction. This work expanded the range of oxidants for the conversion of uric acid to 1,5-diaminoglycoluril. It was found that 1,5-diaminoglycoluril was formed with a yield of 29 % when using equimolar proportions of uric acid and KMnO4. When using MnO2 in a ten times more excess, the yield of 1,5-diaminoglycoluril was 38 %. The article also presents the results of a study of the interaction of uric acid with some amines. The reaction of interaction of uric acid with benzylamine was studied in more detail, the reaction products of which were 4-benzylimino-5-benzylaminoallantoin, 4- benzylimino-1-benzylamino-allantoin and 4-benzyliminoallantoin. Based on the synthesis of 4- benzyliminoallantoin, a number of promising derivatives of 4-iminoallantoin were obtained, namely 4- ethyliminoallantoin, 4-propyliminoallantoin, 4-i-propyliminoallantoin, 4-n-butyliminoallantoin, 4-ibutyliminoallantoin, 4-tert-butyliminoallantoin.