ALKYLATION OF [1,2,4]TRIAZOLO[1,5-<i>a</i>][1,3,5]TRIAZIN-7(3<i>H</i>)-ONES

Authors

  • Ирина В. Ульянкина Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Анна В. Заводская 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 К. Ширяев Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Евгения В. Селезнева Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Владимир В. Бахарев Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

DOI:

https://doi.org/10.1007/3293

Keywords:

5-amino-substituted 3-alkyl[1, 2, 4]triazolo[1, 5-a][1, 3, 5]triazin-7(3Н)-ones, 5-aza analogs of acyclovir, [1, 5]triazines, alkylation

Abstract

The results of pioneering research on the alkylation of fused [1,2,4]triazolo[1,5-a][1,3,5]triazine system are presented, including computational studies of the reaction between 5-dimethylamino[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-one and bromoethane. The reaction of 5-amino-substituted [1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones with allyl bromide, bromoethane, or 2acetoxyethoxymethyl bromide occurred selectively with the formation of products due to alkylation at the N-3 nitrogen atom of the heterocyclic system. The removal of acetyl protecting group from 5-amino-substituted {2-[(7-oxo[1,2,4]triazolo[1,5-a][1,3,5]triazin-3(7Н)-yl)methoxy]ethyl}acetates gave 5-aza analogs of acyclovir, containing a substituted amino group at position 5 of the heterocyclic 3-[(2-hydroxyethoxy)methyl][1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-one system.

Authors: Irina V. Ul'yankina, Anna V. Zavodskaya, Victor E. Parfenov, Alexander A. Gidaspov, Andrey K. Shiryaev, Eugenia V. Selezneva, Vladimir V. Bakharev*

Author Biographies

Ирина В. Ульянкина, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Ирина Владимировна Ульянкина

Анна В. Заводская, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Анна Викторовна Заводская

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 К. Ширяев, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Андрей Константинович Ширяев

Евгения В. Селезнева, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Евгения Валерьевна Селезнева

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

Владимир Валентинович Бахарев

Downloads

Published

2016-12-22

Issue

Vol. 52 No. 12 (2016)

Section

Original Papers