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Abstract <p>A three-component condensation of 4,4,4-trifluoro-1-phenylbutane-1,3-dione with formaldehyde and alkanethiols led to 2-[(alkylsulfanyl)methyl]-4,4,4-trifluoro-1-phenylbutane-1,3-diones, the heterocyclization of which with hydrazine, phenylhydrazine, or benzylhydrazine under heating or microwave irradiation afforded the corresponding 4-(alkylsulfanylmethyl)-substituted 3-(trifluoromethyl)<b>-</b>1<i>H</i>-pyrazoles. The reaction of sulfur-containing 4,4,4-trifluoro-1-phenylbutane-1,3-diones with phenyl- and benzylhydrazine was characterized by high regioselectivity and resulted in the predominant formation of 1-aryl-5-phenyl-3-(trifluoromethyl)-1<i>H</i>-pyrazoles. 2-[(Alkylsulfanyl)methyl]-4,4,4-trifluoro-1-phenylbutane-1,3-diones were unstable and underwent detrifluoroacetylation upon isolation by chromatography to form 3-(alkylsulfanyl)-1-phenylpropan-1-ones.</p>

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Synthesis of Sulfur-Containing Trifluoromethyl-1H-pyrazoles from 4,4,4-Trifluoro-1-phenylbutane-1,3-dione

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • L. A. Baeva,
  • L. F. Biktasheva,
  • R. R. Gataullin,
  • T. R. Nugumanov

摘要

Abstract

A three-component condensation of 4,4,4-trifluoro-1-phenylbutane-1,3-dione with formaldehyde and alkanethiols led to 2-[(alkylsulfanyl)methyl]-4,4,4-trifluoro-1-phenylbutane-1,3-diones, the heterocyclization of which with hydrazine, phenylhydrazine, or benzylhydrazine under heating or microwave irradiation afforded the corresponding 4-(alkylsulfanylmethyl)-substituted 3-(trifluoromethyl)-1H-pyrazoles. The reaction of sulfur-containing 4,4,4-trifluoro-1-phenylbutane-1,3-diones with phenyl- and benzylhydrazine was characterized by high regioselectivity and resulted in the predominant formation of 1-aryl-5-phenyl-3-(trifluoromethyl)-1H-pyrazoles. 2-[(Alkylsulfanyl)methyl]-4,4,4-trifluoro-1-phenylbutane-1,3-diones were unstable and underwent detrifluoroacetylation upon isolation by chromatography to form 3-(alkylsulfanyl)-1-phenylpropan-1-ones.