3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity
Journal of Agricultural and Food Chemistry2009Vol. 57(16), pp. 7422–7426
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Gui Yu, Satori Iwamoto, Lori I. Robins, James C. Fettinger, Thomas C. Sparks, Beth A. Lorsbach, Mark J. Kurth
Abstract
A collection of 91 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides was prepared starting from dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate. The thioether moieties in these compounds were subsequently oxidized to give the corresponding 3-(arylsulfonylmethyl)isoxazole-4,5-dicarboxamides. By carefully controlling stoichiometry and reaction conditions, the C4 and C5 carbomethoxy groups could be differentially derivatized to carboxamides. A total of 182 trisubstituted isoxazoles are reported and deposited in the National Institutes of Health Molecular Repository; an 80 compound subset was evaluated for insecticidal activity.
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