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ANDREA PACE

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.