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

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 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

Fingerprint

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

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

@article{99b1f751af3543d3a998f2f7d35b90f7,

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.",

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.}",

year = "2009",

doi = "10.1021/jf901512t",

language = "English (US)",

volume = "57",

pages = "7422--7426",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - 3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides

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.

PY - 2009

Y1 - 2009

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

UR - http://www.scopus.com/inward/record.url?scp=70349208964&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70349208964&partnerID=8YFLogxK

U2 - 10.1021/jf901512t

DO - 10.1021/jf901512t

M3 - Article

C2 - 19624156

AN - SCOPUS:70349208964

VL - 57

SP - 7422

EP - 7426

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 16

ER -

Access to Document

10.1021/jf901512t