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 › peer-review

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
State	Published - Apr 9 2012

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

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10.1021/co200200u

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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.",

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AU - Dallas, Jerry L.

AU - Kurth, Mark J.

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KW - 1,3-dipolar cycloaddition

KW - Cu(I)-catalyzed azide-alkyne cycloaddition

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

Abstract

Keywords

ASJC Scopus subject areas

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