title: Synthesis of 3-aminoisoxazoles via the addition-elimination of amines on 3-bromoisoxazolines.
abstract: A novel two-step procedure for the synthesis of 3-amino-5-substituted-isoxazoles is described. In the presence of a base, readily available 3-bromoisoxazolines react with amines to afford 3-aminoisoxazolines. An oxidation protocol was developed for these heterocycles to provide 3-aminoisoxazoles in consistently high yield.
authors.affiliation: Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Quebec, Canada H9H 3L1. melina_girardin@merck.com
authors.forename: Mélina
authors.initials: M
authors.lastname: Girardin
authors.forename: Pamela G
authors.initials: PG
authors.lastname: Alsabeh
authors.forename: Sophie
authors.initials: S
authors.lastname: Lauzon
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Dolman
authors.forename: Stéphane G
authors.initials: SG
authors.lastname: Ouellet
authors.forename: Greg
authors.initials: G
authors.lastname: Hughes
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000588:Amines; D006842:Hydrocarbons, Brominated; D007555:Isoxazoles