Synthesis of 3-aminoisoxazoles via the addition-elimination of amines on 3-bromoisoxazolines.
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.
Girardin
Mélina
M
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Quebec, Canada H9H 3L1. melina_girardin@merck.com
Alsabeh
Pamela G
PG
Lauzon
Sophie
S
Dolman
Sarah J
SJ
Ouellet
Stéphane G
SG
Hughes
Greg
G
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
D000588:Amines; D006842:Hydrocarbons, Brominated; D007555:Isoxazoles