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Reactions of polyfluorinated chalcones with o-aminobenzenethiol and its zinc salt

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Abstract

The reactions of polyfluorochalcones with o-aminothiophenol in methanol in the presence of HCl afford polyfluorine-substituted 2,3-dihydrobenzo[b][1,5]thiazepines. In some cases, the cyclization is accompanied by fluorine substitution in the perfluorophenyl ring. Probably, the formation of thiazepines proceeds through the Michael thia-adduct. The Zn salt of o-aminothiophenol reacts with chalcones in DMF exclusively via fluorine substitution.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentéva, Novosibirsk, 630090, Russian Federation

    K. S. Shmuilovich, N. A. Orlova, I. V. Beregovaya & V. V. Shelkovnikov

Authors
  1. K. S. Shmuilovich
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  2. N. A. Orlova
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  3. I. V. Beregovaya
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  4. V. V. Shelkovnikov
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Correspondence to N. A. Orlova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 353–358, February, 2011.

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Shmuilovich, K.S., Orlova, N.A., Beregovaya, I.V. et al. Reactions of polyfluorinated chalcones with o-aminobenzenethiol and its zinc salt. Russ Chem Bull 60, 361–367 (2011). https://doi.org/10.1007/s11172-011-0058-2

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  • DOI: https://doi.org/10.1007/s11172-011-0058-2

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