Abstract
In the chemistry of heterocyclic compounds, bicyclic bisureas — glycolurils, have a special place. Glycolurils are used as a basis for the industrial production of substances that have found application in many areas of human life. The variety of glycoluril derivatives and their properties is primarily due to various substituents in the bicyclic structure. In this review, 2,4,6,8-tetraazabicyclo[3.3.0.]octane-3,7-dione (glycoluril), as the main representative of bicyclic bisureas, its physico-chemical properties, and methods for the synthesis of derivatives based on it are considered. In particular, the main physico-chemical characteristics of glycoluril and the data obtained from its spectral analysis by IR, NMR spectroscopy and X-ray diffraction analysis are presented and discussed. The paper briefly outlines the known methods for the synthesis of glycolurils and related compounds, also highlights the chemical properties of glycoluril and its derivatives, as well as the ways to modify them. Coordination compounds based on N-alkylglycolurils as ligands are briefly considered. The reaction products of N-halogenation and N-acylation of glycolurils are presented and discussed. Reactions for obtaining phosphorus-, nitro- and nitroso derivatives of glycolurils; alkylation methods, Mannich reactions, thionization, alkaline hydrolysis and reduction reactions at the carbonyl group of glycolurils are also shown. There is a discussion of the macromolecules formation in the condensation reaction of glycoluril with formaldehyde as precursors for the synthesis of cucurbit[n]urils.