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. © 2011 The Royal Society of Chemistry.
Martorana, A., Piccionello, A.P., Buscemi, S., Giorgi, G., Pace, A. (2011). Synthesis of 4(5)-Phenacyl-imidazoles from Isoxazole Side-Chain Rearrangements. ORGANIC & BIOMOLECULAR CHEMISTRY, 9(2), 491-496 [10.1039/c0ob00511h].
Synthesis of 4(5)-Phenacyl-imidazoles from Isoxazole Side-Chain Rearrangements
Giorgi, Gianluca;
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. © 2011 The Royal Society of Chemistry.
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https://hdl.handle.net/11365/9999
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