Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements.
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.
Dipartimento Farmacochimico, Tossicologico e Biologico, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy.
Annamaria
A
Martorana
Antonio Palumbo
AP
Piccionello
Silvestre
S
Buscemi
Gianluca
G
Giorgi
Andrea
A
Pace
D000215:Acylation; D007093:Imidazoles / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D007093:Imidazoles; D007097:Imines; D007555:Isoxazoles