OPENING OF THE 1,3,5-TRIAZINE RING IN 3-METHYL-5-(TRINITROMETHYL)TETRAZOLO[1,5-<i>a</i>][1,3,5]TRIAZIN-7-ONE BY THE ACTION OF ALCOHOLS

Authors

  • Владимир В. Бахарев Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Александр А. Гидаспов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Владимир А. Заломленков Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Виктор Е. Парфенов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Ольга В. Головина Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Павел А. Слепухин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620219

DOI:

https://doi.org/10.1007/6538

Keywords:

tetrazolo[1, 5-a][1, 3, 5]triazine, (tetrazolyliminomethyl)carbamates, (tetrazolyl-2, 2, 2-trinitroethyl)carbamates, 1, 5-triazine ring opening, trinitromethyl group substitution

Abstract

It was shown for the first time that in the reaction of 3-methyl-5-(trinitromethyl)tetrazolo[1,5-a][1,3,5]triazin-7-one with alcohols in the presence of bases, along with the expected substitution of the trinitromethyl group, opening of the 1,3,5-triazine ring with the addition of an alcohol at the site of the C–N bond cleavage takes place. It was found that in the absence of bases only opening of the 1,3,5-triazine ring occurs with the formation of alkyl esters of {1-[(1-methyl-1H-tetrazol-5-yl)imino]-2,2,2-trinitroethyl}carbamic acid, and the trinitromethyl group retains high reactivity and can be substituted by the action of alcohols in the presence of a base.

Authors: Vladimir V. Bakharev*, Alexander А. Gidaspov, Vladimir А. Zalomlenkov, Victor E. Parfenov, Olga V. Golovina, Pavel А. Slepukhin

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Published

2022-03-10

Issue

Vol. 58 No. 2/3 (2022)

Section

Short Communications