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Alkylation reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with alkyl halides

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Chemistry of Heterocyclic Compounds Aims and scope

The alkylation reactions of fused tetrazolo[1,5-a][1,3,5]triazine system were studied. The results of quantum-chemical calculations for the reaction of 5-(dimethylamino)tetrazolo[1,5-a][1,3,5]triazin-7(3H)-one with ethyl bromide are presented. The reactions of 5-aminosubstituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with ethyl-, butyl-, and allyl halides led to the formation of products due to alkylation at the N-3 nitrogen atom of the ring system, 3-alkyl-5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones, as well as products due to alkylation at the exocyclic oxygen atom with tetrazole ring opening, 2-amino-substituted 6-alkoxy-4-azido-1,3,5-triazines. Besides that, the product that was alkylated at the ring N-3 nitrogen atom underwent hydrolytic cleavage of the 1,3,5-triazine ring with elimination of the carbonyl functional group and formation of N-(1-alkyl-1H-tetrazol-5-yl)-N'-alkyl- and N-(1-alkyl-1H-tetrazol-5-yl)-N',N'-dialkylguanidines.

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation, within the framework of Project part of State Assignment to the Samara State Technical University (project No. 4.813.2014/K).

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Victor E. Parfenov, Vladimir V. Bakharev, Alexander A. Gidaspov & Andrey K. Shiryaev

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St./ 20 Akademicheskaya St, Yekaterinburg, 620219, Russia

    Pavel A. Slepukhin

  3. Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St, Yekaterinburg, 620002, Russia

    Pavel A. Slepukhin

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  1. Victor E. Parfenov
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  2. Vladimir V. Bakharev
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  3. Alexander A. Gidaspov
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  4. Andrey K. Shiryaev
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  5. Pavel A. Slepukhin
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Correspondence to Vladimir V. Bakharev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(12), 1061–1069

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Parfenov, V.E., Bakharev, V.V., Gidaspov, A.A. et al. Alkylation reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3H)-ones with alkyl halides. Chem Heterocycl Comp 52, 1061–1069 (2016). https://doi.org/10.1007/s10593-017-2007-y

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