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

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

Research output: Contribution to journalArticle

15 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7422-7426
Number of pages5
JournalJournal of Agricultural and Food Chemistry
Volume57
Issue number16
DOIs
StatePublished - 2009

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Keywords

  • Insecticidal activity
  • Isoxazole
  • Nucleophilic selectivity

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

Cite this

Yu, G. J., Iwamoto, S., Robins, L. I., Fettinger, J. C., Sparks, T. C., Lorsbach, B. A., & Kurth, M. J. (2009). 3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity. Journal of Agricultural and Food Chemistry, 57(16), 7422-7426. https://doi.org/10.1021/jf901512t