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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 9, pp 892–901 | Cite as

7-(2-Ethoxyphenyl)dihydroazolopyrimidines in oxidation reactions with bromine

  • Irina G. Ovchinnikova
  • Olga V. Fedorova
  • Gennady L. Rusinov
  • Valery N. Charushin
Article
  • 17 Downloads

This study was focused on the oxidation reactions of 4,7- and 6,7-dihydroazolo[1,5-а]pyrimidines with bromine and mechanisms for such reactions were proposed. The effects of ethoxyphenyl substituent and azole ring on the reaction kinetics were demonstrated. The structures of the main products and intermediates of bromination and oxidation reactions were confirmed by 1H NMR spectroscopy, GCMS analysis, and X-ray structural analysis. It was established that the noticeable tuberculostatic activity of azolo[1,5-а]pyrimidines became considerably weaker in the case of their brominated analogs.

Keywords

brominated derivatives of azolo(azido)pyrimidines bromination oxidation with bromine 

Notes

Acknowledgments

This work received financial support from the Russian Science Foundation (grant No. 15-13-00077-P).

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Irina G. Ovchinnikova
    • 1
  • Olga V. Fedorova
    • 1
  • Gennady L. Rusinov
    • 1
    • 2
  • Valery N. Charushin
    • 1
    • 2
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia
  2. 2.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia

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