

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

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.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv