1H-Imidazole-2-diazonium salts in the synthesis of new benzo[e]imidazo[2,1-c][1,2,4]triazin-6-ols

1H-Imidazole-2-diazonium salts in the synthesis of new benzo[e]imidazo[2,1-c][1,2,4]triazin-6-ols Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2026, Volume: 75, Number: 2, Pages: 559-566 Pages count : 8 DOI: 10.1007/s11172-026-4908-3

Authors

Mangusheva D.A. ¹ , Vandyshev D.Yu. ¹ , Present M.A. ² , Fakhrutdinov A.N. ² , Shestakov A.S. ¹ , Nikitenko D.V. ³ , Shikhaliev Kh.S. ¹

Affiliations

1	Voronezh State University, 1 Universitetskaya pl., 394018, Voronezh, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
3	L. M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, 70 ul. Rosy Luxemburg, 283048, Donetsk, Russian Federation

New benzo[e]imidazo[2,1-c][1,2,4]triazin-6-ols were obtained by the reactions of 1H-imidazole-2-diazonium salts with cyclohexane-1,3-diones. The reaction proceeds through the formation of hydrazones, which, treated with acids, undergo intramolecular cyclization with subsequent oxidative aromatization. The nature of substituents in the imidazole fragment significantly influences the course of the transformations and the choice of optimal reaction conditions. Using dimedone as the methylene-active component allows for the formation of stable tautomeric forms stabilized by electron-withdrawing groups, particularly, by cyano groups at positions 4 and 5 of the imidazole ring.

Mangusheva D.A. , Vandyshev D.Y. , Present M.A. , Fakhrutdinov A.N. , Shestakov A.S. , Nikitenko D.V. , Shikhaliev K.S.
1H-Imidazole-2-diazonium salts in the synthesis of new benzo[e]imidazo[2,1-c][1,2,4]triazin-6-ols
Russian Chemical Bulletin. 2026. V.75. N2. P.559-566. DOI: 10.1007/s11172-026-4908-3 WOS Scopus OpenAlex

Мангушева Д.А. , Вандышев Д.Ю. , Презент М.А. , Фахрутдинов А.Н. , Шестаков А.С. , Никитенко Д.В. , Шихалиев Х.С.
Соли 1H-имидазол-2-диазония в синтезе новых бензо[e]имидазо[2,1-c][1,2,4]триазин-6-олов
Известия Академии наук. Серия химическая. 2026. Т.75. №2. С.559-566.

Submitted:	Jul 6, 2025
Published online:	Apr 11, 2026

≡ Web of science:	WOS:001738024100007
≡ Scopus:	2-s2.0-105035529919
≡ OpenAlex:	W7153465382