Open Access Open Access  Restricted Access Subscription Access


Ирина В. Ульянкина, Анна В. Заводская, Виктор Е. Парфенов, Александр А. Гидаспов, Андрей К. Ширяев, Евгения В. Селезнева, Владимир В. Бахарев
Cover Image


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*


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

Full Text: PDF (Russian) Supplementary File(s): Supporting information (5MB)



Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia -