Synthesis of Polymer-Bound 4-Acetoxy-3-phenylbenzaldehyde Derivatives:Applications in Solid-Phase Organic Synthesis

摘要

Aminomethyl polystyrene resin was reacted with 4-(5'-formyl-2'-hydroxyphenyl)benzoic acid and 4-(5'-formyl-2'-hydroxyphenyl)phenyl propionic acid,respectively,in the presence of 1-hydroxybenzotriazole and 1,3-diisopropylcar-bodiimide to yield polymer-bound benzaldehydes.The phenolic group in resins was acetylated with acetic anhydride to afford two polymer-bound 4-acetoxybenzaldehydes.The reductive amination of polymer-bound linkers by amines and sodium triacetoxyborohydride,followed by sulfonylation with arylsulfonyl chloride derivatives in the presence of pyridine and the cleavage with TFA/DCM/H_2O,produced pure sulfonamides.