Selective nucleophilic chemistry in the synthesis of 5-carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic acids
Selective nucleophilic chemistry in the synthesis of 5-carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic acids
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DOI：
10.1021/cc0601074
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发表时间：
2007-01-01
影响因子：
--
通讯作者：
Kurth, Mark J.
中科院分区：
文献类型：
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作者：
Robins, Lori I.;Fettinger, James C.;Kurth, Mark J.
The solution-phase syntheses of 5-carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic acids were accomplished from dimethyl 3-chloromethylisoxazole-4,5-dicarboxylate by selective nucleophilic chemistry. For example, treatment of this trifunctionalized core with 3-bromobenzylamine and subsequent X-ray analysis identified the sole product as methyl 5-(3-bromobenzylcarbamoyl)-3-chloromethylisoxazole-4-carboxylate. Subjecting this amide/ester to thiophenol in the presence of 1 N NaOH completed the two-step transformation of this versatile starting material to the targeted 5-carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic acid. Employing various amines and thiophenols, this chemistry was applied in the generation of a 90-compound library of druglike isoxazoles.
