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3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity

Journal of Agricultural and Food Chemistry, ISSN: 0021-8561, Vol: 57, Issue: 16, Page: 7422-7426
2009
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Article Description

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. © 2009 American Chemical Society.

Bibliographic Details

Yu, Gui J; Iwamoto, Satori; Robins, Lori I; Fettinger, James C; Sparks, Thomas C; Lorsbach, Beth A; Kurth, Mark J

American Chemical Society (ACS)

Chemistry; Agricultural and Biological Sciences

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