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

doi:10.1021/jf901512t

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

Chemistry

Research output: Contribution to journal › Article › peer-review

18 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 language	English (US)
Pages (from-to)	7422-7426
Number of pages	5
Journal	Journal of Agricultural and Food Chemistry
Volume	57
Issue number	16
DOIs	https://doi.org/10.1021/jf901512t
State	Published - 2009

Keywords

Insecticidal activity
Isoxazole
Nucleophilic selectivity

ASJC Scopus subject areas

Agricultural and Biological Sciences(all)
Chemistry(all)

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10.1021/jf901512t

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3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides : Chemoselective Nucleophilic Chemistry and Insecticidal Activity. / Yu, Gui J.; Iwamoto, Satori; Robins, Lori I.; Fettinger, James C.; Sparks, Thomas C.; Lorsbach, Beth A.; Kurth, Mark J.

In: Journal of Agricultural and Food Chemistry, Vol. 57, No. 16, 2009, p. 7422-7426.

Research output: Contribution to journal › Article › peer-review

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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.",

keywords = "Insecticidal activity, Isoxazole, Nucleophilic selectivity",

author = "Yu, {Gui J.} and Satori Iwamoto and Robins, {Lori I.} and Fettinger, {James C.} and Sparks, {Thomas C.} and Lorsbach, {Beth A.} and Kurth, {Mark J.}",

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T2 - Chemoselective Nucleophilic Chemistry and Insecticidal Activity

AU - Yu, Gui J.

AU - Iwamoto, Satori

AU - Robins, Lori I.

AU - Fettinger, James C.

AU - Sparks, Thomas C.

AU - Lorsbach, Beth A.

AU - Kurth, Mark J.

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N2 - 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.

AB - 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.

KW - Insecticidal activity

KW - Isoxazole

KW - Nucleophilic selectivity

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

Abstract

Keywords

ASJC Scopus subject areas

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