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Abstract <p>Perfluorobiacetyl reacted with thiourea, <i>N</i>-methylthiourea, and <i>N</i>-phenylthiourea in acetonitrile to give 92–95% of <i>cis</i>/<i>trans</i>-isomeric 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione and 1-methyl­(phenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thiones. The reaction of 4,5-dihy­droxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with 2-aminoethanol produced sulfanylideneimidazothiazolone, whereas the expected imidazooxazinethione was formed as a minor product. An unusual pathway was observed in the reaction of <i>N</i>-methylimidazolidine-2-thione with 2-aminoethanol, which afforded thiohydantoins, 5-[(2-hydroxyethyl)amino]-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one and 5-hydroxy-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one. <i>N</i>-Methylsulfanylideneimidazooxazolone and <i>N</i>-methyl(trifluoromethyl)thiohydantoin were formed instead of the expected thioglycoluril derivative in the reaction of <i>N</i>-methylimidazolidine-2-thione with urea. Heating of 4,5-dihydroxy-1-phenyl-4,5-bis(tri­fluoro­methyl)imidazolidine-2-thione with urea, 2-aminoethanol, or 2-aminophenol in <i>N</i>,<i>N</i>-dimethylacetamide led to the formation of intramolecular rearrangement product, <i>N</i>-phenyl-bis(trifluoromethyl)thiohydantoin.</p>

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Synthesis of Trifluoromethyl-Substituted Imidazolidine-2-thiones and Their Reactions with Urea, 2-Aminoethanol, and 2-Aminophenol

  • 期刊论文

  • 发表日期：

    2025年7月1日

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  • L. V. Saloutina,
  • M. I. Kodess,
  • I. N. Ganebnykh,
  • V. I. Saloutin,
  • O. N. Chupakhin

摘要

Abstract

Perfluorobiacetyl reacted with thiourea, N-methylthiourea, and N-phenylthiourea in acetonitrile to give 92–95% of cis/trans-isomeric 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione and 1-methyl­(phenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thiones. The reaction of 4,5-dihy­droxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with 2-aminoethanol produced sulfanylideneimidazothiazolone, whereas the expected imidazooxazinethione was formed as a minor product. An unusual pathway was observed in the reaction of N-methylimidazolidine-2-thione with 2-aminoethanol, which afforded thiohydantoins, 5-[(2-hydroxyethyl)amino]-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one and 5-hydroxy-3-methyl-2-sulfanylidene-5-(trifluoromethyl)imidazolidin-4-one. N-Methylsulfanylideneimidazooxazolone and N-methyl(trifluoromethyl)thiohydantoin were formed instead of the expected thioglycoluril derivative in the reaction of N-methylimidazolidine-2-thione with urea. Heating of 4,5-dihydroxy-1-phenyl-4,5-bis(tri­fluoro­methyl)imidazolidine-2-thione with urea, 2-aminoethanol, or 2-aminophenol in N,N-dimethylacetamide led to the formation of intramolecular rearrangement product, N-phenyl-bis(trifluoromethyl)thiohydantoin.