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Two series of isoxazoles substituted by long alkyl or alkenyl chains in the α position with respect to the oxygen atom or in the α position with respect to the two heteroatoms have been synthesized. Starting from 3,5-dimethylisoxazole, the regioselective metalation/alkylation on the α-O methyl group was a very convenient route to a large variety of "α-O substituted isoxazoles". When applied to α-O methylated isoxazoles bearing an α-N alkenyl chain the same method provides an original unequivocal approach to 3,5-dialkenyl isoxazoles. An alternative route to these compounds, despite the formation of di-isoxazoline as by-product and an additional step corresponding to the oxidation of the intermediate isoxazoline, is the 1,3-dipolar cycloaddition, by using terminal dienes as dipolarophiles with alkenyl dipoles. Nevertheless, the cycloaddition between monoalkylated alcynes and alkylated dipoles remains the most straightforward synthesis of 3,5-dialkyl isoxazoles. Key words: isoxazoles, alkenyl side chains, metalation–alkylation, regioselectivity.

Synthèse d'isoxazoles substitués en α de l'oxygène et d'isoxazoles substitués en α de l'azote et de l'oxygène par des chaînes alkyle ou alcényle