The photochemistry of six N3-(3-fluoro-4-dialkylaminophenyl)-oxazolidinones known for their antimicrobial activity has been examined. All of these compounds are defluorinated in water (dec ≈ 0.25) and in methanol (dec ≈ 0.03), reasonably via the triplet. The chemical processes observed are reductive defluorination and solvolysis, depending on the structural variation introduced (thus, tethering the dialkylamino group to the aromatic ring and introducing a highly polar group in the oxazolidinone moiety have an effect). A likely mechanism involves the fragmentation of the C-F bond yielding the corresponding triplet phenyl cation. This intermediate either is reduced or, under appropriate conditions, intersystem crosses to the singlet state that adds the solvent.

Photochemistry of oxazolidinones antibacterial drugs

FASANI, ELISA;TILOCCA, FEDELE;ALBINI, ANGELO
2009-01-01

Abstract

The photochemistry of six N3-(3-fluoro-4-dialkylaminophenyl)-oxazolidinones known for their antimicrobial activity has been examined. All of these compounds are defluorinated in water (dec ≈ 0.25) and in methanol (dec ≈ 0.03), reasonably via the triplet. The chemical processes observed are reductive defluorination and solvolysis, depending on the structural variation introduced (thus, tethering the dialkylamino group to the aromatic ring and introducing a highly polar group in the oxazolidinone moiety have an effect). A likely mechanism involves the fragmentation of the C-F bond yielding the corresponding triplet phenyl cation. This intermediate either is reduced or, under appropriate conditions, intersystem crosses to the singlet state that adds the solvent.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/209029
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