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 | |
| State | Published - 2009 |
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Keywords
- Insecticidal activity
- Isoxazole
- Nucleophilic selectivity
ASJC Scopus subject areas
- Agricultural and Biological Sciences(all)
- Chemistry(all)
Cite this
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
}
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 -