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

Yulia V. Khoroshunova, Denis A. Morozov, Andrey I. Taratayko, Polina D. Gladkikh, Yuri I. Glazachev, Igor A. Kirilyuk

Research output: Contribution to journalArticlepeer-review


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).

Original languageEnglish
Pages (from-to)2036-2042
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Publication statusPublished - 27 Aug 2019


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

Fingerprint Dive into the research topics of 'Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition'. Together they form a unique fingerprint.

Cite this