3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: chemoselective nucleophilic chemistry and insecticidal activity.

3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: chemoselective nucleophilic chemistry and insecticidal activity.
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DOI:
10.1021/jf901512t
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发表时间:
2009-08-26
影响因子:
6.1
通讯作者:
Kurth MJ
Kurth MJ
中科院分区:
农林科学1区
文献类型:
--
作者:
Yu GJ;Iwamoto S;Robins LI;Fettinger JC;Sparks TC;Lorsbach BA;Kurth MJ

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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.
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