ALKYLATION OF 5-DIMETHYLAMINOTETRAZOLO[1,5-<i>a</i>][1,3,5]TRIAZIN-7-ONE

Authors

  • Владимир В. Бахарев Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Виктор Е. Парфенов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Александр А. Гидаспов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Андрей А. Пименов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Павел А. Слепухин I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch, Russian Academy of Sciencies, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620219
  • Кирилл Ю. Супоницкий A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciencies, 28 Vavilov St., Moscow 119991

DOI:

https://doi.org/10.1007/2604

Keywords:

tetrazolo[1, 5-a][1, 3, 5]triazines, alkylation, ambident nucleophiles, anomalous nucleosides, tetrazolylguanidines

Abstract

Reaction of 5-dimethylaminotetrazolo[1,5-а][1,3,5]triazin-7-one tetrabutylammonium salt with allyl bromide in acetonitrile proceeds with the formation of 3-allyl-5-dimethylaminotetrazolo[1,5-a][1,3,5]triazin-7-one (N-alkylation), 6-allyloxy-4-azido-N,N-dimethyl-1,3,5-triazin-2-amine (O-alkylation), and 2-(1-allyl-1H-tetrazol-5-yl)-1,1-dimethylguanidine as the product of hydrolysis of N-alkylated tetrazolo[1,5-a][1,3,5]triazin-7-one. The structure of the reaction products was confirmed by IR, 1H and 13C NMR spectroscopy as well as elemental and X-ray structural analysis data.

How to Cite
Bakharev, V. V.; Parfenov, V. E.; Gidaspov, A. A.; Pimenov, A. A.; Slepukhin, P. A.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2015, 51, 745. [Khim. Geterotsikl. Soedin. 2015, 51, 745.]

For this article in the English edition see DOI 10.1007/s10593-015-1768-4

Author Biographies

Владимир В. Бахарев, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Владимир Валентинович Бахарев

Виктор Е. Парфенов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Виктор Евгеньевич Парфенов

Александр А. Гидаспов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Александр Александрович Гидаспов

Андрей А. Пименов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Андрей Александрович Пименов

Павел А. Слепухин, I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch, Russian Academy of Sciencies, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620219

Павел Александрович Слепухин

Кирилл Ю. Супоницкий, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciencies, 28 Vavilov St., Moscow 119991

Кирилл Юрьевич Супоницкий

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Published

2015-09-11

Issue

Vol. 51 No. 8 (2015)

Section

Original Papers