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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 2(9), p. 491-496, 2011

DOI: 10.1039/c0ob00511h

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Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements

Journal article published in 2011 by Annamaria Martorana, Antonio Palumbo Piccionello, Silvestre Buscemi, Gianluca Giorgi, Andrea Pace ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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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.