Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis

J Org Chem. 2006 Sep 29;71(20):7915-8. doi: 10.1021/jo061328z.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Benzaldehydes / chemical synthesis*
  • Benzoic Acid / chemistry
  • Cross-Linking Reagents / chemistry
  • Polystyrenes / chemistry
  • Propionates / chemistry
  • Resins, Synthetic / chemistry
  • Sulfonamides / chemical synthesis*

Substances

  • Benzaldehydes
  • Cross-Linking Reagents
  • Polystyrenes
  • Propionates
  • Resins, Synthetic
  • Sulfonamides
  • Benzoic Acid
  • propionic acid