title: Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis.
abstract: 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.
authors.affiliation: Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, The University of Rhode Island, Kingston, Rhode Island 02881, USA.
authors.forename: Anil
authors.initials: A
authors.lastname: Kumar
authors.forename: Guofeng
authors.initials: G
authors.lastname: Ye
authors.forename: Yousef
authors.initials: Y
authors.lastname: Ahmadibeni
authors.forename: Keykavous
authors.initials: K
authors.lastname: Parang
mesh_terms: 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*
chemical_list: D001547:Benzaldehydes; D003432:Cross-Linking Reagents; D011137:Polystyrenes; D011422:Propionates; D012117:Resins, Synthetic; D013449:Sulfonamides; D019817:Benzoic Acid; C029658:propionic acid