Construction of a 2 H -1,4-selenazin-3(4 H )-one framework via cyclization of pyrazole derivatives bearing chloroacetamide and selenocyanate fragments

Construction of a 2 H -1,4-selenazin-3(4 H )-one framework via cyclization of pyrazole derivatives bearing chloroacetamide and selenocyanate fragments Научная публикация

Журнал

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2026, Том: 24, Номер: 17, Страницы: 3748-3758 Страниц : 11 DOI: 10.1039/d6ob00263c

Авторы

Kudryavtseva Tatiana A. ¹ , Kudryavtseva Ekaterina N. ¹ , Lichitsky Boris V. ¹

Организации

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr. 47, Moscow 119991, Russian Federation

For the first time, we developed an efficient three-step method for the synthesis of substituted 1,7-dihydropyrazolo[4,3-b][1,4]selenazin-6(5H)-ones starting from readily accessible 5-aminopyrazoles. The presented approach is based on preliminary preparation of chloroacetamide derivatives followed by selenocyanation of the pyrazole ring and final reductive cyclization. The key selenocyanation stage includes the employment of commercially available SeO2 and malononitrile for the generation of triselenium dicyanide in situ in a simple setup under open-air conditions. The elaborated general protocol allowed us to obtain a set of final pyrazoloselenazinones with yields up to 88%. 77Se NMR-monitoring was applied for a detailed investigation of selenocyanation and intramolecular cyclization steps. Mechanistic studies showed that the conclusive reductive stage proceeds through the corresponding diselenide intermediate.

Kudryavtseva T.A. , Kudryavtseva E.N. , Lichitsky B.V.
Construction of a 2 H -1,4-selenazin-3(4 H )-one framework via cyclization of pyrazole derivatives bearing chloroacetamide and selenocyanate fragments
Organic & Biomolecular Chemistry. 2026. V.24. N17. P.3748-3758. DOI: 10.1039/d6ob00263c WOS Scopus OpenAlex

Поступила в редакцию:	13 февр. 2026 г.
Принята к публикации:	9 апр. 2026 г.
Опубликована в печати:	14 апр. 2026 г.
Опубликована online:	6 мая 2026 г.

≡ Web of science:	WOS:001744968700001
≡ Scopus:	2-s2.0-105036273773
≡ OpenAlex:	W7154305755