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Synthesis 2004(16): 2678-2684  
DOI: 10.1055/s-2004-831212
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Synthetic Approach for the Preparation of Imidazole N 3-Oxide

Hugo Cerecetto*a, Alejandra Gerpea, Mercedes González*a, Yolanda Fernández Sainzb, Oscar E. Piroc, Eduardo E. Castellanod
a Department of Organic Chemistry, Faculty of Chemistry/Faculty of Sciences, University of the Republic, 11400 Montevideo, Uruguay
Fax: +598(2)5250749; e-Mail: hcerecet@fq.edu.uy; e-Mail: megonzal@fq.edu.uy;
b Facultad de Ciencias, Pz/Misael Bañuelos s/n, Universidad de Burgos, Burgos, Spain
c Department of Physic, University National of La Plata, 1900 La Plata, Argentina
d Institute of Physics, University of São Paulo, 13560 São Carlos, Brazil
Further Information

Publication History

Received 30 April 2004
Publication Date:
16 September 2004 (online)

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Abstract

A new synthetic procedure of 1-alkyl(aryl)-1H-4-methylimidazole N 3-oxide derivatives by cyclocondensation of α-amine­oximes and orthoesters was studied. Low yields in the cyclization process were the result of predominant Z-stereoisomer around the oxime moiety of α-amineoxime reactants. Different attempts to improve these yields were assayed, mild conditions being those that produce the best results. Also, the special acidity of hydrogen-2 in the imidazole N 3-oxide system was studied in solution by NMR spectroscopy. This property provides a convenient intermediate to access 2-substituted analogues.

Keywords

imidazole N-oxide - cyclization - H-2 acidity

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