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Facile Synthesis of Carboxamide-Substituted 1,3,4-Thiadiazines and 5,6-Dihydro-4H-1,3,4-Thiadiazin-5-Ols

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Chemistry of Heterocyclic Compounds Aims and scope

Novel 2-carboxamide-substituted 1,3,4-thiadiazines and 5,6-dihydro-4H-1,3,4-thiadiazin-5-ols were synthesized by the reaction of oxamic acid thiohydrazides with phenacyl bromides. This reaction was performed using an equimolar mixture of thiohydrazide and α-bromoacetophenones in methanol under basic conditions. The ratio of products obtained in the cyclocondensation was found to be strongly dependent on the substitution pattern and reaction conditions.

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Acknowledgements

The research is supported by the Russian Science Foundation (grant 18-33-00913 мол_а).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Anna S. Komendantova, Ksenya A. Ivanova, Yulia A. Volkova & Igor V. Zavarzin

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., GSP-1, Moscow, 119991, Russia

    Konstantin V. Lyssenko

  3. Plekhanov Russian University of Economics, 36 Stremyannyy Pereulok, Moscow, 117997, Russia

    Konstantin V. Lyssenko

Authors
  1. Anna S. Komendantova
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  2. Ksenya A. Ivanova
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  3. Konstantin V. Lyssenko
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  4. Yulia A. Volkova
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  5. Igor V. Zavarzin
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Corresponding author

Correspondence to Yulia A. Volkova.

Additional information

Supplementary information file containing NMR spectra of compounds 5, 6, and 7, synthesis of starting materials, results of X-ray crystallographic analysis is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 665–671

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Komendantova, A.S., Ivanova, K.A., Lyssenko, K.V. et al. Facile Synthesis of Carboxamide-Substituted 1,3,4-Thiadiazines and 5,6-Dihydro-4H-1,3,4-Thiadiazin-5-Ols. Chem Heterocycl Comp 55, 665–671 (2019). https://doi.org/10.1007/s10593-019-02514-5

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  • DOI: https://doi.org/10.1007/s10593-019-02514-5

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