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

Authors

Anil Kumar, University of Rhode Island
Guofeng Ye, University of Rhode Island
Yousef Ahmadibeni, University of Rhode Island
Keykavous Parang, University of Rhode IslandFollow

Document Type

Article

Date of Original Version

2006

Department

Biomedical and Pharmaceutical Sciences

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.

Citation/Publisher Attribution

Kumar, A., Ye, G., Ahmadibeni, Y., & Parang, K. (2006). Synthesis of Polymer-Bound 4-Acetoxy-3-phenylbenzaldehyde Derivatives:  Applications in Solid-Phase Organic Synthesis. J. Org. Chem. 71(20), 7915-7918. doi: 10.1021/jo061328z

Available at: https://doi.org/10.1021/jo061328z