Unusual formation of imidazooxazolone in the reaction of 1-[(2-acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH

Glycolurils — tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-diones — have found widespread applications in various fields of science and technology. Among them, there are pharmacologically active compounds (antibacterial, nootropic, neurotropic agents, etc.), explosives, gelators, etc. They are used as building blocks in supramolecular chemistry. Therefore, the development of new methods for the synthesis of glycolurils and their analogues has constantly attracted the attention of researchers. In this review, we analyze various approaches to the synthesis of glycolurils and their analogues. The review covers both classical reactions of ureas and related compounds with α-dicarbonyl compounds or with 4,5-dihydroxyimida-zolidin-2-ones (-thiones) and their imino analogues and new original reactions of 4,5-dihydroxyimidazolidin-2-ones (-thiones), imidazolinones and their bicyclic analogues with ureas and KNCS in the presence of acids, condensations of 1,4-disubstituted 1,4-diaza-1,3-dienes with isocyanic and/or isothiocyanic acids or isocyanates, triazine ring contraction in imidazotriazines to give the imidazolidine ring, and transformations of urazoles. The bibliography includes 129 references.

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Advances in the synthesis of heterocycles bearing an endocyclic urea moiety

Smolobochkin¹,

Газизов²,

Бурилов³

et al. 2021

Russ. Chem. Rev.

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The review systematizes and summarizes data on the synthesis of structurally diverse cyclic ureas published over the last 10 years. Saturated and unsaturated monocyclic ureas, as well as fused heterocycles containing one urea moiety, are considered. Data on the biological activity of selected compounds of this type are provided. The synthetic approaches to cyclic carbamides are classified in terms of the reaction type and the source of a carbonyl group. The bibliography includes 235 references.

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Unusual formation of imidazooxazolone in the reaction of 1-[(2-acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH

Cited by 3 publications

References 20 publications

Synthesis of trifluoromethyl – containing oxo(thioxo)imidazothiazolones and thioglycolurils based on perfluorobiacetyl

Synthesis of trifluoromethyl – containing oxo(thioxo)imidazothiazolones and thioglycolurils based on perfluorobiacetyl

Synthesis of glycolurils and their analogues

Advances in the synthesis of heterocycles bearing an endocyclic urea moiety

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