Issue 2, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Annamaria Martorana,a   Antonio Palumbo Piccionello,*b   Silvestre Buscemi,b   Gianluca Giorgic  and  Andrea Paceb  

* Corresponding authors

a Dipartimento Farmacochimico, Tossicologico e Biologico, Università degli Studi di Palermo, Via Archirafi 32, Italy

b Dipartimento di Chimica Organica “E. Paternò”, Università degli Studi di Palermo, Viale delle Scienze - Parco d'Orleans II, Italy
E-mail: apalumbo@unipa.it
Fax: +39 091 596825
Tel: +39 091 596903

c Dipartimento di Chimica, Università degli Studi di Siena, Via Aldo Moro, Italy

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.

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

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Article information

DOI
https://doi.org/10.1039/C0OB00511H
Article type
Paper
Submitted
29 Jul 2010
Accepted
30 Sep 2010
First published
26 Oct 2010

Org. Biomol. Chem., 2011,9, 491-496

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

A. Martorana, A. P. Piccionello, S. Buscemi, G. Giorgi and A. Pace, Org. Biomol. Chem., 2011, 9, 491 DOI: 10.1039/C0OB00511H

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