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Selective Nucleophilic Chemistry in the Synthesis of 5-Carbamoyl-3-sulfanylmethylisoxazole-4-carboxylic Acids.
- Source :
-
Journal of Combinatorial Chemistry . Jan2007, Vol. 9 Issue 1, p139-142. 4p. - Publication Year :
- 2007
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15204766
- Volume :
- 9
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Journal of Combinatorial Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23925886
- Full Text :
- https://doi.org/10.1021/cc0601074