Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis.
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-diisopropylcarbodiimide 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/H2O, produced pure sulfonamides.
Kumar
Anil
A
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, The University of Rhode Island, Kingston, Rhode Island 02881, USA.
Ye
Guofeng
G
Ahmadibeni
Yousef
Y
Parang
Keykavous
K
D001547:Benzaldehydes / Q000138:chemical synthesis*; D019817:Benzoic Acid / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry; D011422:Propionates / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis*
D001547:Benzaldehydes; D003432:Cross-Linking Reagents; D011137:Polystyrenes; D011422:Propionates; D012117:Resins, Synthetic; D013449:Sulfonamides; D019817:Benzoic Acid; C029658:propionic acid