ALKYLATION REACTIONS OF 5-AMINOSUBSTITUTED TETRAZOLO[1,5-<i>a</i>][1,3,5]TRIAZIN-7(3<i>Н</i>)-ONES WITH ALKYL HALIDES

Authors

  • Виктор Е. Парфенов Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Владимир В. Бахарев Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Александр А. Гидаспов Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Андрей К. Ширяев Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Павел А. Слепухин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St., 20 Akademicheskaya St., Ekaterinburg 620219 Ural Federal University named after the first President of Russia B. N. Yeltsin 19 Mira St., Ekaterinburg 620002

DOI:

https://doi.org/10.1007/3393

Keywords:

3-alkyl-5-aminotetrazolo[1, 5-a][1, 3, 5]triazin-7(3Н)-ones, N-(1-alkyl-1H-tetrazol-5-yl)-N'-alkylguanidine, N-(1-alkyl-1H-tetrazol-5-yl)-N', N'-dialkylguanidines, 2-amino-6-alkoxy-4-azido-1, 5-triazines, tetrazolo[1, 5]triazines, alkylation, cleavage of 1, 5-triazine ring

Abstract

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(3Н)-one with ethyl bromide are presented. The reactions of 5-amino-substituted tetrazolo[1,5-a][1,3,5]triazin-7(3Н)-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.

Authors: Victor E. Parfenov, Vladimir V. Bakharev*, Alexander A. Gidaspov, Andrei K. Shiryaev, Pavel A.  Slepukhin

Author Biographies

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

Виктор Евгеньевич Парфенов

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

Владимир Валентинович Бахарев

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

Александр Александрович Гидаспов

Андрей К. Ширяев, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Андрей Константинович Ширяев

Павел А. Слепухин, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St., 20 Akademicheskaya St., Ekaterinburg 620219 Ural Federal University named after the first President of Russia B. N. Yeltsin 19 Mira St., Ekaterinburg 620002

Павел Александрович Слепухин

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Published

2016-12-22

Issue

Vol. 52 No. 12 (2016)

Section

Original Papers