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- Title
Oxidation of quinolones with peracids (an in situ EPR study).
- Authors
Staško, Andrej; Milata, Viktor; Barbieriková, Zuzana; Brezová, Vlasta
- Abstract
4-Oxoquinoline derivatives (quinolones) represent heterocyclic compounds with a variety of biological activities, along with interesting chemical reactivity. The quinolone derivatives possessing secondary amino hydrogen at the nitrogen of the enaminone system are oxidized with 3-chloroperbenzoic acid to nitroxide radicals in the primary step while maintaining their 4-pyridone ring. Otherwise, N-methyl substituted quinolones also form nitroxide radicals coupled with the opening of the 4-pyridone ring in a gradual oxidation of the methyl group via the nitrone-nitroxide spin-adduct cycle. This was confirmed in an analogous oxidation using N, N-dimethylaniline as a model compound. N-Ethyl quinolones in contrast to its N-methyl analog form only one nitroxide radical without a further degradation. Copyright © 2013 John Wiley & Sons, Ltd.
- Subjects
QUINOLONE antibacterial agents; OXIDATION; PEROXY acids; PERACETIC acid; NITROXIDES; NITROGEN oxides
- Publication
Magnetic Resonance in Chemistry, 2014, Vol 52, Issue 1/2, p22
- ISSN
0749-1581
- Publication type
Article
- DOI
10.1002/mrc.4029