3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity
| Autor: | James C. Fettinger, Thomas C. Sparks, Gui J. Yu, Lori I. Robins, Mark J. Kurth, Beth A. Lorsbach, Satori Iwamoto |
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| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Reaction conditions
Insecticides Insecta Molecular Structure Chemistry General Chemistry Isoxazoles Article chemistry.chemical_compound Structure-Activity Relationship Thioether Nucleophile Molecule Structure–activity relationship Organic chemistry Animals Isoxazole General Agricultural and Biological Sciences Selectivity Stoichiometry |
| Popis: | A collection of ninety-one 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides were 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. |
| Databáze: | OpenAIRE |
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