UV-assisted rearrangement of substituted 3-arylaminopyrazoles with an allomaltol fragment into tricyclic cyclopenta[4,5]pyrrolo[2,3-c]pyrazole derivatives Научная публикация
| Журнал |
Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539 |
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| Вых. Данные | Год: 2025, Том: 23, Номер: 28, Страницы: 6738-6744 Страниц : 7 DOI: 10.1039/d5ob00796h | ||
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Реферат:
In the present study, we report a novel photochemical rearrangement of substituted 3-arylaminopyrazoles incorporating an allomaltol fragment. Under UV-irradiation, these compounds undergo ESIPT-induced contraction of the pyran-4-one ring, leading to an unstable α-hydroxy-1,2-diketone intermediate. For the first time, this transient intermediate was successfully trapped via intramolecular cyclization involving the nitrogen atom of the aniline moiety. Using this UV-induced cascade transformation, a facile method for the synthesis of tricyclic cyclopenta[4,5]pyrrolo[2,3-c]pyrazole derivatives was elaborated. The applicability of the designed approach was demonstrated by the preparation of 14 photoproducts with yields up to 78%. The structures of the representative starting pyrazole and one of the target photoproducts were unambiguously confirmed by X-ray analysis.
Библиографическая ссылка:
Komogortsev A.N.
, Milyutin C.V.
, Lichitsky B.V.
, Migulin V.A.
UV-assisted rearrangement of substituted 3-arylaminopyrazoles with an allomaltol fragment into tricyclic cyclopenta[4,5]pyrrolo[2,3-c]pyrazole derivatives
Organic & Biomolecular Chemistry. 2025. V.23. N28. P.6738-6744. DOI: 10.1039/d5ob00796h WOS Scopus OpenAlex
UV-assisted rearrangement of substituted 3-arylaminopyrazoles with an allomaltol fragment into tricyclic cyclopenta[4,5]pyrrolo[2,3-c]pyrazole derivatives
Organic & Biomolecular Chemistry. 2025. V.23. N28. P.6738-6744. DOI: 10.1039/d5ob00796h WOS Scopus OpenAlex
Идентификаторы БД:
| Web of science: | WOS:001520396500001 |
| Scopus: | 2-s2.0-105009749157 |
| OpenAlex: | W4411872738 |