3-(Arylthiomethyl) isoxazole-4, 5-dicarboxamides: chemoselective nucleophilic chemistry and insecticidal activity

GJ Yu, S Iwamoto, LI Robins, JC Fettinger…

Index: Yu, Gui J.; Iwamoto, Satori; Robins, Lori I.; Fettinger, James C.; Sparks, Thomas C.; Lorsbach, Beth A.; Kurth, Mark J. Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 16 p. 7422 - 7426

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Citation Number: 10

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 ...