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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

Abstract: 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
Cite: 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 OpenAlex
Files: Full text from publisher
Dates:
Published online: Aug 27, 2019
Identifiers:
Web of science: WOS:000482964800001
Scopus: 2-s2.0-85072554339
Elibrary: 41639937
OpenAlex: W2948923309
Citing:
DB Citing
Scopus 6
Web of science 7
OpenAlex 6
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