A novel base-induced rearrangement of isoxazoles into imidazole derivatives is reported. In the isoxazole series, this represents the first example of a three-atom side-chain rearrangement involving a CNC sequence. The reactions are carried out under nitrogen and produced 2-aryl-4(5)-phenacyl-5(4)-phenyl-imidazoles in high yields. In the presence of oxygen, a cascade rearrangement-oxidation reaction sequence was observed and imidazole derivatives bearing an oxidized side-chain were isolated.
Martorana, A., Palumbo Piccionello, A., Buscemi, S., Giorgi, G., Pace, A. (2011). Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements. ORGANIC & BIOMOLECULAR CHEMISTRY, 9(9), 491-496 [10.1039/c0ob00511h].
Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements
MARTORANA, Annamaria;PALUMBO PICCIONELLO, Antonio;BUSCEMI, Silvestre;PACE, Andrea
2011-01-01
Abstract
A novel base-induced rearrangement of isoxazoles into imidazole derivatives is reported. In the isoxazole series, this represents the first example of a three-atom side-chain rearrangement involving a CNC sequence. The reactions are carried out under nitrogen and produced 2-aryl-4(5)-phenacyl-5(4)-phenyl-imidazoles in high yields. In the presence of oxygen, a cascade rearrangement-oxidation reaction sequence was observed and imidazole derivatives bearing an oxidized side-chain were isolated.
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