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  • Title: Selective nucleophilic chemistry in the synthesis of 5-carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic acids.
    Author: Robins LI, Fettinger JC, Tinti DS, Kurth MJ.
    Journal: J Comb Chem; 2007; 9(1):139-42. PubMed ID: 17206842.
    Abstract:
    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.
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