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■ Reaction of 4-Bromobenzyl-3-methyl-1,2-oxazin-6-ones with Primary Aliphatic Amines. Synthesis and Structural Determination of New Oxazine and Isoxazole Derivatives

Monique Bebot, Pascal Coudert, Fernand Leal, Jacques Métin, Vincent Gaumet, Sylvie Mavel,Catherine Rubat, and Jacques Couquelet*

*Laboratoire de Chimie Organique Thérapeutique, Groupe de Recherche en Pharmacochimie, Faculté de Pharmacie, Université de Clermont I, 28, Place Henri Dunant, B.P. 38, 63001 Clermont-Ferrand Cedex, France

Abstract

Reaction of 4-bromobenzyl-6H-1,2-oxazin-6-ones (1) with aminoalkylamines furnished a mixture of 5-aminoalkylamino-6H-1,2-oxazine-6-ones (2), 4-(aminoalkylaminocarbonylmethyl)isoxazoles (3) and 5-(aminoalkylaminocarbonyl)isoxazoles (4) which were separated by column chromatography. Structure of all derivatives was determined by ¹H- and ¹³C -NMR methods, including INEPT measurements. Structure of isoxazoles (3) and (4) was confirmed by X-Ray analysis. In addition, test compounds were investigated for analgesic and antidepressant activities in mice.