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

Authors

  • Сергей А. Серков N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Марина А. Еськова N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia
  • Наталья В. Сигай N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Наталия Н. Костикова N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Татьяна Н. Вольхина A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russia
  • Наталья Г. Колотыркина N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Галина А. Газиева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

DOI:

https://doi.org/10.1007/6161

Keywords:

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

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.

Author Biographies

Сергей А. Серков, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

лаборатория химии нитросоединений, научный сотрудник

Марина А. Еськова, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia

аспирант

Наталья В. Сигай, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

лаборатория химии нитросоединений, научный сотрудник

Наталия Н. Костикова, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

лаборатория химии нитросоединений, инженер-исследователь

Наталья Г. Колотыркина, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

отдел структурных исследований, старший научный сотрудник

Галина А. Газиева, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

Russian Academy of sciences

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Published

2021-06-19

Issue

Vol. 57 No. 6 (2021)

Section

Original Papers