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Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine Научная публикация

Журнал Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Вых. Данные Год: 2025, Том: 184, Номер статьи : 134782, Страниц : DOI: 10.1016/j.tet.2025.134782
Авторы Izmest'ev Alexei N. 1 , Isakov Sergey S. 2,1 , Strelenko Yuri A. 1 , Kravchenko Angelina N. 1 , Gazieva Galina A. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2 D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russian Federation

Реферат: Four series of dispiro-fused polyheterocyclic compounds containing spiro(pyrrolidine-2,3′-oxindole) and imidazothiazolotriazine moieties were prepared by [3 + 2] cycloaddition of azomethine ylide to ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine. It was shown that ylide cycloaddition occurs to both diastereotopic faces of the dipolarophiles to give the target compounds as two diastereomers. Skeletal rearrangement of the major dispiro(imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidin-2′,3″-oxindoles) (anti-exo-diastereomers) gave isomeric dispiro(imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidin-2′,3″-oxindoles) (angular syn-exo-diastereomers) that are inaccessible by the direct [3 + 2] cycloaddition reaction.
Библиографическая ссылка: Izmest'ev A.N. , Isakov S.S. , Strelenko Y.A. , Kravchenko A.N. , Gazieva G.A.
Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine
Tetrahedron. 2025. V.184. 134782 . DOI: 10.1016/j.tet.2025.134782 WOS Scopus OpenAlex
Идентификаторы БД:
≡ Web of science: WOS:001518606900006
≡ Scopus: 2-s2.0-105008019335
≡ OpenAlex: W4411306643
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