title: Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines.
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.
authors.affiliation: Department of Chemistry, University of California, Davis, California 95616, United States.
authors.forename: Keith C
authors.initials: KC
authors.lastname: Coffman
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Hartley
authors.forename: Jerry L
authors.initials: JL
authors.lastname: Dallas
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D057166:High-Throughput Screening Assays; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; D010880:Piperidines; D011728:Pyridones; D054852:Small Molecule Libraries; D003300:Copper