Photochemical Approach to Fused Quinoxaline Derivatives From Allomaltol‐Containing Terarylenes With 2‐Aminooxazole Bridge Fragment via Trapping of Unstable Cyclopentene‐1,2‐Dione Intermediates

Photochemical Approach to Fused Quinoxaline Derivatives From Allomaltol‐Containing Terarylenes With 2‐Aminooxazole Bridge Fragment via Trapping of Unstable Cyclopentene‐1,2‐Dione Intermediates Научная публикация

Журнал

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Вых. Данные

Год: 2026, Том: 63, Номер: 10, Страницы: 1601-1610 Страниц : 10 DOI: 10.1002/jhet.70232

Авторы

Migulin Alexander V. ¹ , Migulin Vasily A. ¹ , Milyutin Constantine V. ¹ , Komogortsev Andrey N. ¹

Организации

1	Russian Academy of Sciences N. D. Zelinsky Institute of Organic Chemistry Moscow Russia

The photochemical behavior of terarylenes bearing allomaltol and 2-aminooxazole fragments has been investigated, providing the basis for an efficient strategy toward substituted cyclopenta[b]quinoxalines. Upon irradiation of starting compounds with 400 nm visible light, the allomaltol moiety undergoes selectively ESIPT-induced contraction of the pyranone ring, affording highly reactive α-hydroxycyclopentene-1,2-dione intermediates, as evidenced by 1H NMR monitoring. Notably, the free amino group does not inhibit the photorearrangement, in contrast to related amino-substituted terarylenes. In situ trapping with 1,2-phenylenediamines affords cyclopenta[b]quinoxaline derivatives in yields of up to 87%, while phenylhydrazine gives separable E/Z hydrazones. The one-pot protocol proceeds under mild, metal- and base-free conditions.

Migulin A.V. , Migulin V.A. , Milyutin C.V. , Komogortsev A.N.
Photochemical Approach to Fused Quinoxaline Derivatives From Allomaltol‐Containing Terarylenes With 2‐Aminooxazole Bridge Fragment via Trapping of Unstable Cyclopentene‐1,2‐Dione Intermediates
Journal of Heterocyclic Chemistry. 2026. V.63. N10. P.1601-1610. DOI: 10.1002/jhet.70232 WOS Scopus OpenAlex

Поступила в редакцию:	4 июн. 2026 г.
Принята к публикации:	7 авг. 2026 г.
Опубликована в печати:	20 авг. 2026 г.
Опубликована online:	20 авг. 2026 г.

≡ Web of science:	WOS:001853300600001
≡ Scopus:	2-s2.0-105047716979
≡ OpenAlex:	W7203763191