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

  • Anna S. Komendantova
  • Ksenya A. Ivanova
  • Konstantin V. Lyssenko
  • Yulia A. VolkovaEmail author
  • Igor V. Zavarzin
Article
  • 9 Downloads

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.

Keywords

5,6-dihydro-4H-[1,3,4]thiadiazin-5-ols oxamic acid thiohydrazides phenacyl bromide 1,3,4-thiadiazines cyclocondensation 

Notes

Acknowledgements

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

Supplementary material

10593_2019_2514_MOESM1_ESM.pdf (851 kb)
ESM 1 (PDF 851 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Anna S. Komendantova
    • 1
  • Ksenya A. Ivanova
    • 1
  • Konstantin V. Lyssenko
    • 2
    • 3
  • Yulia A. Volkova
    • 1
    Email author
  • Igor V. Zavarzin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of SciencesMoscowRussia
  2. 2.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of SciencesMoscowRussia
  3. 3.Plekhanov Russian University of EconomicsMoscowRussia

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