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

Anil Kumar, Guofeng Ye, Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 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/H 2O, produced pure sulfonamides.

Original languageEnglish (US)
Pages (from-to)7915-7918
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number20
DOIs
StatePublished - Sep 29 2006
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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