Synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils

Sergei А. Serkov,Marina А. Es’kova,Natalya V. Sigay,Natalya N. Kostikova,Tatyana N. Volkhina,Natalya G. Kolotyrkina,Galina А. Gazieva

CHEMISTRY OF HETEROCYCLIC COMPOUNDS（2021）

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Abstract

method for the synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils was developed based on nucleophilic substitution of the sulfur atom with the oxygen atom in the corresponding thioglycolurils via alkylation of the latter followed by acid hydrolysis of alkylsulfanyl derivatives of thioglycolurils, both with the isolation of alkylsulfanyl intermediates and by the one-pot method. The structure of the synthesized compounds was confirmed by X-ray structural analysis of several examples.

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Key words

5-[(4-bromobenzyl)sulfanyl]-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2 (1H)-ones, glycolurils, 5-methylsulfanyl-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2(1H)-ones, tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-diones, thioglycolurils, 5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones, S-alkylation, hydrolysis

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