REGIOSELECTIVE SYNTHESIS OF 1-ALKYL-4-METHYLSEMITHIOGLYCOLURILS

Authors

  • Антон А. Галочкин N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991
  • Алиса Е. Павловская N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991 Mendeleyev University of Chemical Technology of Russia, Miusskaya pl. 9, Moscow 125047
  • Владимир В. Баранов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991
  • Юрий А. Стреленко N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991
  • Ангелина Н. Кравченко N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991

DOI:

https://doi.org/10.1007/7068

Keywords:

4, 5-dihydroxy-1-imidazolidine-2-thione, ureas, semithioglycolurils, thioureas, regioselective synthesis

Abstract

The regioselective reaction of 4,5-dihydroxy-1-methylimidazolidine-2-thione with 1-alkylureas was explored for the first time, providing the previously inaccessible 1-alkyl-4-methylsemithioglycolurils as the major products. We demonstrated that the interaction of the reactants was accompanied by the formation of isomeric 1-alkyl-6-methylsemithioglycolurils and several known compounds: 1-methyl- and 3-methylthiohydantoins, 1-methyl-1H-imidazole-2(3H)-thione, and 1,4-disubstituted glycolurils as minor products. The reaction of 4,5-dihydroxy-1-methylimidazolidine-2-thione with 1-isopropylurea also produced a mixture of 1,1'(1-methyl-2-thioxoimidazolidine-4,5-diyl)bis(3-isopropylurea) diastereomers.

Authors: Anton A. Galochkin*, Alisa E. Pavlovskaya, Vladimir V. Baranov,
Yuri A. Strelenko, Angelina N. Kravchenko

 

Author Biography

Антон А. Галочкин, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991

Research Engineer of Nitrogen containing compounds Lab

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Published

2022-11-17

Issue

Vol. 58 No. 11 (2022)

Section

Original Papers