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

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


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; [1,2,4]triazolo[1,5-a][1,3,5]triazines; alkylation

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


 

 

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