Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements
- Authors: Martorana, A; Palumbo Piccionello, A; Buscemi, S; Giorgi, G; Pace, A
- Publication year: 2011
- Type: Articolo in rivista (Articolo in rivista)
- Key words: Heterocyclic rearrangement, isoxazole, imidazole, tandem reactions.
- OA Link: http://hdl.handle.net/10447/54620
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.