Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via Intramolecular 1,3-Dipolar Cycloaddition

  1. Yulia V. Khoroshunova,
  2. Denis A. Morozov ORCID Logo,
  3. Andrey I. TarataykoORCID Logo,
  4. Polina D. Gladkikh,
  5. Yuri I. Glazachev and
  6. Igor A. KirilyukORCID Logo

Submitting author affiliation: N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Novosibirsk, Russian Federation

Beilstein Arch. 2019, 201937. doi:10.3762/bxiv.2019.37.v1

Published 03 Jun 2019

  • Preprint

Abstract

Sterically shielded nitroxides of pyrrolidine series are known to demonstrate the highest stability to reduction. Here we report on the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of pent-4-enyl group to nitrone atom followed by intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. Kinetics of reduction of the new nitroxides with ascorbate was studied and compared to that 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: Aldonitrones; 1,3-dipolar cycloaddition; DMPO; pyrrolidine nitroxides; sterically shielded nitroxides.

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Khoroshunova, Y. V.; Morozov, D. A.; Taratayko, A. I.; Gladkikh, P. D.; Glazachev, Y. I.; Kirilyuk, I. A. Beilstein Arch. 2019, 201937. doi:10.3762/bxiv.2019.37.v1

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