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Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition. / Khoroshunova, Yulia V.; Morozov, Denis A.; Taratayko, Andrey I. et al.

In: Beilstein Journal of Organic Chemistry, Vol. 15, 27.08.2019, p. 2036-2042.

Research output: Contribution to journal › Article › peer-review

Harvard

Khoroshunova, YV, Morozov, DA, Taratayko, AI, Gladkikh, PD, Glazachev, YI & Kirilyuk, IA 2019, 'Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition', Beilstein Journal of Organic Chemistry, vol. 15, pp. 2036-2042. https://doi.org/10.3762/bjoc.15.200

APA

Khoroshunova, Y. V., Morozov, D. A., Taratayko, A. I., Gladkikh, P. D., Glazachev, Y. I., & Kirilyuk, I. A. (2019). Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition. Beilstein Journal of Organic Chemistry, 15, 2036-2042. https://doi.org/10.3762/bjoc.15.200

Vancouver

Khoroshunova YV, Morozov DA, Taratayko AI, Gladkikh PD, Glazachev YI, Kirilyuk IA. Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition. Beilstein Journal of Organic Chemistry. 2019 Aug 27;15:2036-2042. doi: 10.3762/bjoc.15.200

Author

Khoroshunova, Yulia V. ; Morozov, Denis A. ; Taratayko, Andrey I. et al. / Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition. In: Beilstein Journal of Organic Chemistry. 2019 ; Vol. 15. pp. 2036-2042.

BibTeX

@article{5c836796119345e3a0895116d5446863,
title = "Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition",
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).",
keywords = "1,3-dipolar cycloaddition, 1-pyrroline-N-oxide, Aldonitrone, Pyrrolidine nitroxides, Sterically shielded nitroxide",
author = "Khoroshunova, {Yulia V.} and Morozov, {Denis A.} and Taratayko, {Andrey I.} and Gladkikh, {Polina D.} and Glazachev, {Yuri I.} and Kirilyuk, {Igor A.}",
year = "2019",
month = aug,
day = "27",
doi = "10.3762/bjoc.15.200",
language = "English",
volume = "15",
pages = "2036--2042",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

AU - Khoroshunova, Yulia V.

AU - Morozov, Denis A.

AU - Taratayko, Andrey I.

AU - Gladkikh, Polina D.

AU - Glazachev, Yuri I.

AU - Kirilyuk, Igor A.

PY - 2019/8/27

Y1 - 2019/8/27

N2 - 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).

AB - 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).

KW - 1,3-dipolar cycloaddition

KW - 1-pyrroline-N-oxide

KW - Aldonitrone

KW - Pyrrolidine nitroxides

KW - Sterically shielded nitroxide

UR - http://www.scopus.com/inward/record.url?scp=85072554339&partnerID=8YFLogxK

U2 - 10.3762/bjoc.15.200

DO - 10.3762/bjoc.15.200

M3 - Article

C2 - 31501671

AN - SCOPUS:85072554339

VL - 15

SP - 2036

EP - 2042

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 21609978