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Synthesis of 1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide and its methyl derivatives

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Abstract

1H-[1,2,3]Triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide (3) was synthesized by reduction of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide (1) with PCl3, reduction of 1-methoxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide (4) with Na2S2O4, and by the reaction of compound 4 with Et3N. Both methylation of compound 3 with diazomethane and reaction of Ag-salt of compound 3 with MeI occur at the triazole cycle to give all three possible isomers. The structures of the synthesized compounds were confirmed by 1H, 13C, 14N, and 15N NMR spectroscopy.

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Authors and Affiliations

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

    A. A. Voronin, V. P. Zelenov, A. M. Churakov, Yu. A. Strelenko & V. A. Tartakovsky

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  1. A. A. Voronin
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  2. V. P. Zelenov
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  3. A. M. Churakov
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  4. Yu. A. Strelenko
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  5. V. A. Tartakovsky
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Correspondence to A. M. Churakov.

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Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0699—0703, March, 2015.

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Voronin, A.A., Zelenov, V.P., Churakov, A.M. et al. Synthesis of 1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide and its methyl derivatives. Russ Chem Bull 64, 699–703 (2015). https://doi.org/10.1007/s11172-015-0922-6

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  • DOI: https://doi.org/10.1007/s11172-015-0922-6

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