title: 3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: chemoselective nucleophilic chemistry and insecticidal activity.
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.
authors.affiliation: Department of Chemistry, University of California, Davis, California 95616, USA.
authors.forename: Gui J
authors.initials: GJ
authors.lastname: Yu
authors.forename: Satori
authors.initials: S
authors.lastname: Iwamoto
authors.forename: Lori I
authors.initials: LI
authors.lastname: Robins
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Thomas C
authors.initials: TC
authors.lastname: Sparks
authors.forename: Beth A
authors.initials: BA
authors.lastname: Lorsbach
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D000818:Animals; D007313:Insecta / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D007555:Isoxazoles