Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition Научная публикация
| Журнал |
Beilstein Journal of Organic Chemistry
ISSN: 1860-5397 |
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| Вых. Данные | Год: 2019, Том: 15, Страницы: 2036-2042 Страниц : 7 DOI: 10.3762/bjoc.15.200 | ||||||
| Ключевые слова | 1,3-dipolar cycloaddition; 1-pyrroline-N-oxide; Aldonitrone; Pyrrolidine nitroxides; Sterically shielded nitroxide | ||||||
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Реферат:
Sterically shielded nitroxides of the pyrrolidine series have shown the highest resistance to reduction. Here we report the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were studied and compared to those of previously published (1S,2R,3′S,4′S,5′S,2″R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2′-(3′,4′-di-tert-butoxy)pyrrolidine-5′,1″-(2″-hydroxymethyl)cyclopentane]-1′-oxyl (1). © 2019 Khoroshunova et al
Библиографическая ссылка:
Khoroshunova Y.V.
, Morozov D.A.
, Taratayko A.I.
, Gladkikh P.D.
, Glazachev Y.I.
, Kirilyuk I.A.
Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition
Beilstein Journal of Organic Chemistry. 2019.
V.15. P.2036-2042. DOI: 10.3762/bjoc.15.200
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Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition
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| Опубликована online: | 27 авг. 2019 г. |
Идентификаторы БД:
| Web of science: | WOS:000482964800001 |
| Scopus: | 2-s2.0-85072554339 |
| РИНЦ: | 41639937 |
| OpenAlex: | W2948923309 |