Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines

Keith C. Coffman, Timothy P. Hartley, Jerry L. Dallas, Mark J. Kurth

Research output: Contribution to journalArticle

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Abstract

Practical and efficient methods have been developed for the diversity-oriented synthesis of isoxazolodihydropyridinones via the 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. A select few of these isoxazolodihydropyridinones were further elaborated with triazoles by copper-catalyzed azide-alkyne cycloaddition reactions. A total of 70 compounds and intermediates were synthesized and analyzed for drug likeness. Sixty-four of these novel compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.

Original languageEnglish (US)
Pages (from-to)280-284
Number of pages5
JournalACS Combinatorial Science
Volume14
Issue number4
DOIs
StatePublished - Apr 9 2012

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Keywords

  • 1,3-dipolar cycloaddition
  • Cu(I)-catalyzed azide-alkyne cycloaddition
  • heterocycle
  • isoxazole, triazole

ASJC Scopus subject areas

  • Chemistry(all)

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