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Pummerer Reactions of Thiopyran Derivatives as a Method for the Preparation of Trifluoro-Methyl-Substituted Thiolanes with Antiviral Activity

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Chemistry of Heterocyclic Compounds Aims and scope

2-(p-Tolylsulfanyl)-2-trifluoromethyl-3,6-dihydro-2Н-thiopyran 1-oxides undergo a vinylogous Pummerer reaction upon interaction with trifluoroacetic anhydride, forming 2-(p-tolylsulfanyl)-4-tri-fluoroacetoxy-2-trifluoromethyl-3,4-dihydro-2Н-thiopyrans. The hydrolysis, acetylation, and free radical desulfanylation of these compounds with a subsequent oxidation of the sulfur atom leads to 4-acetoxy-2-trifluoromethyl-3,4-dihydro-2Н-thiopyran 1-oxides. The Pummerer addition reaction of the latter with acetic anhydride and boron trifluoride etherate results in a ring contraction and formation of 3-acet-oxy-2-diacetoxymethyl-5-(trifluoromethyl)thiolanes, which could be converted with sodium boro-hydride to 3-hydroxy-2-hydroxymethyl-5-(trifluoromethyl)thiolanes having antiviral activity.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02094, Ukraine

    S. A. Siry, V. M. Timoshenko & Yu. G. Vlasenko

  2. D. K. Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, 154 Acad. Zabolotnoho St., Kyiv, D03680, Ukraine

    G. V. Baranova, S. D. Zagorodnya & N. V. Nesterova

Authors
  1. S. A. Siry
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  2. V. M. Timoshenko
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  3. Yu. G. Vlasenko
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  4. G. V. Baranova
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  5. S. D. Zagorodnya
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  6. N. V. Nesterova
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Correspondence to V. M. Timoshenko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 513-526, April, 2014.

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Siry, S.A., Timoshenko, V.M., Vlasenko, Y.G. et al. Pummerer Reactions of Thiopyran Derivatives as a Method for the Preparation of Trifluoro-Methyl-Substituted Thiolanes with Antiviral Activity. Chem Heterocycl Comp 50, 467–478 (2014). https://doi.org/10.1007/s10593-014-1497-0

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  • DOI: https://doi.org/10.1007/s10593-014-1497-0

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