Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

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

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

Авторы

Khoroshunova Y.V. ^1,2 , Morozov D.A. ¹ , Taratayko A.I. ^1,2 , Gladkikh P.D. ^1,2 , Glazachev Y.I. ³ , Kirilyuk I.A. ^1,2

Организации

1	(Scopus) N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk, 630090, Russian Federation
2	(Scopus) Novosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russian Federation
3	(Scopus) Voevodsky Institute o Chemical Kinetics and Combustion SB RAS, Institutskaya 3, Novosibirsk, 630090, Russian Federation

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

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 WOS Scopus РИНЦ

Полный текст от издателя

Опубликована online:

27 авг. 2019 г.

Web of science	WOS:000482964800001
Scopus	2-s2.0-85072554339
РИНЦ	41639937
OpenAlex	W2948923309