Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

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 piperid...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2020-05, Vol.25 (10), p.2430
Main Authors: Isbera, Mostafa, Bognár, Balázs, Jekő, József, Sár, Cecilia, Hideg, Kálmán, Kálai, Tamás
Format: Article
Language:English
Subjects:
Alkenes - chemistry
antioxidant activity
Antioxidants
Bisphosphonates
Carbon - chemistry
Horner-Wadsworth-Emmons olefination
Molecular Structure
Nitrogen Oxides - chemical synthesis
Nitrogen Oxides - chemistry
nitroxides
Organic compounds
Organic phosphorus
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Organophosphorus compounds
Oxidation
Phosphonates
Phosphorus
Phosphorus compounds
Piperidine
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
Substitution reactions
Vitamin E
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Summary: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 well-established methods, such as the Pudovik, Arbuzov and Horner-Wadsworth-Emmons (HWE) reactions. The reaction of paramagnetic a-bromoketone produced a vinylphosphonate in the Perkow reaction. Paramagnetic a-hydroxyphosphonates 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 carbon-carbon bond-forming reactions in the Horner-Wadsworth-Emmons 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 a-hydroxyphosphonatate nitroxides exhibited remarkable antioxidant activity.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25102430