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SYNTHESIS OF 1,3-DIALKYL-4-[(ARYLMETHYLIDENE)AMINO]GLYCOLURILS

Сергей А. Серков, Марина А. Еськова, Наталья В. Сигай, Наталия Н. Костикова, Татьяна Н. Вольхина, Наталья Г. Колотыркина, Галина А. Газиева
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Abstract


A 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.

Keywords


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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