THE FEATURES OF THE MICHAEL REACTION IN ([1,2,4]TRIAZOLO[4,3-<i>a</i>][1,3,5]TRIAZIN-5-YL)DINITROMETHANIDES

Authors

  • Ольга В. Головина Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Виктор Е. Парфенов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Павел А. Слепухин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620219, Russia
  • Дмитрий В. Хакимов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Алексей Б. Шереметев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Владимир В. Бахарев Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

DOI:

https://doi.org/10.1007/6848

Keywords:

dinitromethanides, [1, 2, 4]triazolo[4, 3-a][1, 3, 5]triazines, Michael reaction, regioselectivity, zwitterionic polynitrogen dinitroheterocycles.

Abstract

The Michael addition of activated alkenes to ([1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl)dinitromethanides in the presence of K2HPO4 leads regioselectively to N1-alkylation products. The structure of [7-(dimethylamino)-1-(3-oxobutyl)[1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl]-dinitromethanide was established by X-ray structural analysis. The features of the reactivity of dinitromethanides are explained with quantum-chemical methods.

 

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Published

2022-10-21

Issue

Vol. 58 No. 10 (2022): Chemistry of polyheteroatomic heterocyclic systems

Section

Original Papers