Syntheses and reactions of pyrroline, piperidine nitroxide phosphonates

Mostafa Isbera, Balázs Bognár, József Jekő, Cecilia Sár, Kálmán Hideg, Tamás Kálai

Research output: Contribution to journalArticle

Abstract

Organophosphorus compounds occupy a significant position among the plethora of organic compounds, but a limited number of paramagnetic phosphorus compounds have been reported, including paramagnetic phosphonates. This paper describes the syntheses and further transformations of pyrroline and piperidine nitroxide phosphonates by wellestablished methods, such as the Pudovik, Arbuzov and HornerWadsworthEmmons (HWE) reactions. The reaction of paramagnetic αbromoketone produced a vinylphosphonate in the Perkow reaction. Paramagnetic αhydroxyphosphonates could be subjected to oxidation, elimination and substitution reactions to produce various paramagnetic phosphonates. The synthesized paramagnetic phosphonates proved to be useful synthetic building blocks for carboncarbon bondforming reactions in the Horner-WadsworthEmmons olefination reactions. The unsaturated compounds achieved could be transformed into various substituted pyrroline nitroxides, proxyl nitroxides and paramagnetic polyaromatics. The Trolox® equivalent antioxidant capacity (TEAC) of new phosphonates was also screened, and tertiary αhydroxyphosphonatate nitroxides exhibited remarkable antioxidant activity.

Original languageEnglish
Article number2430
JournalMolecules
Volume25
Issue number10
DOIs
Publication statusPublished - May 2020

Keywords

  • Antioxidant activity
  • HornerWadsworthEmmons olefination
  • Nitroxides
  • Phosphonates

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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