Selective nucleophilic chemistry in the synthesis of 5-carbamoyl-3- sulfanylmethylisoxazole-4-carboxylic acids

Lori I. Robins, James C. Fettinger, Dino S. Tinti, Mark J. Kurth

Research output: Contribution to journalArticle

7 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)139-142
Number of pages4
JournalJournal of Combinatorial Chemistry
Volume9
Issue number1
DOIs
StatePublished - Jan 2007

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

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