The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides

The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides Научная публикация

Журнал

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

Вых. Данные

Год: 2025, Том: 23, Страницы: 369-376 Страниц : 8 DOI: 10.1039/d4ob01570c

Авторы

Bakuleva Nadezhda A. ¹ , Lichitskii Boris V. ¹ , Komogortsev Andrey N. ¹ , Tretyakov Evgeny V. ¹

Организации

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

For the first time, the photochemical behavior of aryl-substituted 2,3-dihydropyrazine 1,4-dioxides was investigated. A common feature of all observed photoprocesses is the conversion of nitrone moieties into an oxaziridine ring to give substituted bi- or polycyclic systems. It was shown that the direction of the reaction depends on the irradiation wavelength and the employed solvent. For instance, the use of 365 nm UV light leads to the cyclization of both nitrone moieties. In contrast, visible-light irradiation (450 nm) allows one to regiospecifically utilize an aldonitrone unit to form 7-oxa-1,4-diazabicyclo[4.1.0]hept-4-ene 4-oxide derivatives. Generally, the oxaziridine ring possesses high reactivity and can be transformed in situ by various reagents. The molecular and crystal structures of the representatives of both bicyclic systems were solved for the first time with X-ray diffraction analysis.

Bakuleva N.A. , Lichitskii B.V. , Komogortsev A.N. , Tretyakov E.V.
The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides
Organic and Biomolecular Chemistry. 2025. V.23. P.369-376. DOI: 10.1039/d4ob01570c WOS OpenAlex

Web of science:	WOS:001357852000001
OpenAlex:	W4404497996

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