Application of aryloximes as solid-phase ketone linkers.
In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-bound oximes followed by subsequent cyclorelease to give ketone product in good yields and purities. [reaction--see text]
Lepore
Salvatore D
SD
Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285, USA. slepore@fau.edu
Wiley
Michael R
MR
D003500:Cyclization; D006868:Hydrolysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*
D007659:Ketones; D009570:Nitriles; D010091:Oximes