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Halo-heterocyclization of butenyl(prenyl)thioethers of 4,5-diphenyl-1,2,4-triazol-3-thiole into triazolo[5,1-b] [1,3]thiazinium systems: experimental and theoretical evolution

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Abstract

A facile and highly efficient regioselective synthesis of partially saturated triazolo[5,1-b][1,3]thiazinium salts by the electrophilic heterocyclization of the butenyl thioethers of 4,5-diphenyl-1,2,4-triazol-3-thiol with halogens was developed. Under developed conditions, electrophilic cyclization reactions proceeded smoothly and cleanly and the corresponding fused products were obtained in high yields in all cases examined. Herein, we also report the studying of the regiochemistry of this process using computer simulation methods, XDR, and spectral investigations for explaining of electrophilic cyclization mechanism and solving of final products structure.

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Acknowledgements

This work was supported by the Ministry of Education and Science of Ukraine (Project GR-0119U100232).

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Authors and Affiliations

  1. Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod, 88000, Ukraine

    Nataliya Korol, Mikhail Slivka, Maksym Fizer & Vasyl Lendel

  2. SSI “Institute for Single Crystals” NASU, Nauky ave. 60, Kharkiv, 61001, Ukraine

    Vjacheslav Baumer

Authors
  1. Nataliya Korol
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  2. Mikhail Slivka
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  3. Maksym Fizer
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  4. Vjacheslav Baumer
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  5. Vasyl Lendel
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Correspondence to Nataliya Korol.

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Korol, N., Slivka, M., Fizer, M. et al. Halo-heterocyclization of butenyl(prenyl)thioethers of 4,5-diphenyl-1,2,4-triazol-3-thiole into triazolo[5,1-b] [1,3]thiazinium systems: experimental and theoretical evolution. Monatsh Chem 151, 191–198 (2020). https://doi.org/10.1007/s00706-019-02545-w

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