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

Ольга В. Головина, Виктор Е. Парфенов, Павел А. Слепухин, Дмитрий В. Хакимов, Алексей Б. Шереметев, Владимир В. Бахарев
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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.

 


Keywords


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

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