The features of the Michael reaction in ([1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl)dinitromethanides

The features of the Michael reaction in ([1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl)dinitromethanides Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2022, Volume: 58, Number: 10, Pages: 506-513 Pages count : 8 DOI: 10.1007/s10593-022-03120-8

Authors

Golovina Olga V. ¹ , Parfenov Victor E. ¹ , Slepukhin Pavel А. ² , Khakimov Dmitry V. ³ , Sheremetev Aleksei B. ³ , Bakharev Vladimir V. ¹

Affiliations

1	Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
2	Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620219, Russia
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russi

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.

Golovina O.V. , Parfenov V.E. , Slepukhin P.А. , Khakimov D.V. , Sheremetev A.B. , Bakharev V.V.
The features of the Michael reaction in ([1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl)dinitromethanides
Chemistry of Heterocyclic Compounds. 2022. V.58. N10. P.506-513. DOI: 10.1007/s10593-022-03120-8 WOS Scopus OpenAlex

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