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

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

doi:10.1021/co200200u

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

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

Chemistry

Research output: Contribution to journal › Article

12 Scopus citations

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 language	English (US)
Pages (from-to)	280-284
Number of pages	5
Journal	ACS Combinatorial Science
Volume	14
Issue number	4
DOIs	https://doi.org/10.1021/co200200u
Publication status	Published - 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)

Cite this

Coffman, K. C., Hartley, T. P., Dallas, J. L., & Kurth, M. J. (2012). Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. ACS Combinatorial Science, 14(4), 280-284. https://doi.org/10.1021/co200200u

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10.1021/co200200u