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.
Keywords: EPR spectroscopy; N,N-dimethylaniline; nitroxide; oxidation; peracids; quinolones.
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