Solution phase synthesis of a diverse library of highly substituted isoxazoles.
The iodocyclization of O-methyloximes of 2-alkyn-1-ones affords 4-iodoisoxazoles, which undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles. The palladium-catalyzed processes have been adapted to parallel synthesis utilizing commercially available boronic acid, acetylene, styrene, and amine sublibraries. Accordingly, a diverse 51-member library of 3,4,5-trisubstituted isoxazoles has been generated.
Waldo
Jesse P
JP
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Mehta
Saurabh
S
Neuenswander
Benjamin
B
Lushington
Gerald H
GH
Larock
Richard C
RC
D000114:Acetylene / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D007555:Isoxazoles / Q000138:chemical synthesis*; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry
D000588:Amines; D001897:Boronic Acids; D007555:Isoxazoles; D012996:Solutions; D020058:Styrene; D010165:Palladium; D000114:Acetylene