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PHOTOLYTIC REARRANGEMENT OF METRONIDAZOLE TO 1‐HYDROXYETHYL‐2‐METHYL‐4‐HYDROXYIMINO‐5‐OXO‐IMIDAZOLE AND THE FORMATION OF COPPER COMPLEXES OF THESE COMPOUNDS

Abstract— A labile intermediate in the photolytic rearrangement of the antibacterial drug, metronidazole, was identified by isolating the product of photolysis of metronidazole benzoate in methanol. The intermediate, 1‐hydroxyethyl‐2‐methyl‐4‐hydroxyimino‐5‐oxo‐imidazole, was shown to act as a bidentate chelating agent for copper(II) ions, whereas metronidazole forms a weak monodentate complex. The intermediate may be relevant to the bioactivation mechanism of metronidazole.