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Synthesis of 2-polyfluoroalkyl-2,3-dihydro-1,3,4-thiadiazoles via regioselective [3+2] cycloaddition of nitrile imines to polyfluoroalkanethioamides

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Chemistry of Heterocyclic Compounds Aims and scope

[3+2] Cycloaddition reactions of polyfluoroalkanethioamides with nitrile imines, generated in situ by dehydrochlorination of the corresponding hydrazonoyl chlorides, in the presence of triethylamine, were studied. A new method was proposed on the basis of these reactions for the synthesis of 2-polyfluoroalkyl-2,3-dihydro-1,3,4-thiadiazoles.

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Notes

  1. Signals of the predominant isomer are denoted with one asterisk (*), the signals of both diastereomers – with two asterisks (**).

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murman’ska St., Kyiv, 02660, Ukraine

    Sergiy S. Mykhaylychenko, Nadezhda V. Pikun, Eduard B. Rusanov, Alexander B. Rozhenko & Yuriy G. Shermolovich

Authors
  1. Sergiy S. Mykhaylychenko
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  2. Nadezhda V. Pikun
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  3. Eduard B. Rusanov
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  4. Alexander B. Rozhenko
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  5. Yuriy G. Shermolovich
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Correspondence to Yuriy G. Shermolovich.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1268–1276

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Mykhaylychenko, S.S., Pikun, N.V., Rusanov, E.B. et al. Synthesis of 2-polyfluoroalkyl-2,3-dihydro-1,3,4-thiadiazoles via regioselective [3+2] cycloaddition of nitrile imines to polyfluoroalkanethioamides. Chem Heterocycl Comp 53, 1268–1276 (2017). https://doi.org/10.1007/s10593-018-2199-9

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  • DOI: https://doi.org/10.1007/s10593-018-2199-9

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