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 Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2019, Volume: 15, Pages: 2036-2042 Pages count : 7 DOI: 10.3762/bjoc.15.200

Tags

1,3-dipolar cycloaddition; 1-pyrroline-N-oxide; Aldonitrone; Pyrrolidine nitroxides; Sterically shielded nitroxide

Authors

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

Affiliations

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

Full text from publisher

Published online:

Aug 27, 2019

Web of science	WOS:000482964800001
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