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Synthesis of bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazine, a novel polynitrogenated heterocyclic system

Abstract

2-Aryl [1,2,4]triazolo[1,5-d][1,2,4]triazine-5(6H)-thiones were methylated using methyl iodide in the presence of NaOH to give the corresponding 5-methylthio derivatives. Upon treatment with hydrazine hydrate, the latter were transformed to the corresponding 5-hydrazino derivatives via nucleophilic displacement. The 5-hydrazino compounds were reacted with orthoesters to furnish a novel heterocyclic system, bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazines.

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Acknowledgments

We acknowledge the financial support from Research Council of Islamic Azad University, Tonekabon branch and Alzahra University, Tehran, Iran.

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Correspondence to Majid M. Heravi.

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Montazeri, N., Heravi, M.M., Tajfirooz, F. et al. Synthesis of bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazine, a novel polynitrogenated heterocyclic system. Monatsh Chem 148, 691–694 (2017). https://doi.org/10.1007/s00706-016-1810-y

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  • DOI: https://doi.org/10.1007/s00706-016-1810-y

Keywords

  • Bis-triazolotriazine
  • Triazolotriazine
  • Orthoester
  • Cyclizations
  • Heterocycles