The Solid-Phase Zincke Reaction: Preparation of ω-Hydroxy Pyridinium Salts in the Search for CFTR Activation

2000/07/22 by Masahiro Eda, Mark J. Kurth, Michael H. Nantz · 1 citation
Biochemistry, Genetics and Molecular Biology · Medicine · #Adenosine and Purinergic Signaling #Advanced biosensing and bioanalysis techniques #Cystic Fibrosis Research Advances

paper · doi:10.1021/jo0001636

openalex publication_date 2000/07/22 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/15

Abstract

A study of structural modifications of MPB-07 was undertaken as part of a synthetic program aimed at discovering small molecules with CFTR activation potential. Solid-phase synthesis techniques were used to prepare derivatives of MPB-07 employing the Zincke reaction for the construction of aromatic, quaternary ammonium salts such as those found in 2 or 3. In this transformation, primary amines react with highly electrophilic N-2,4-dinitrophenylpyridinium (DNP) salt 4 to afford pyridinium salt 8 with release of 2,4-dinitroaniline 6. Thus, the reaction of 1-(2,4-dinitrophenyl)pyridinium salts with various polymer-bound amino ethers, followed by cleavage from the resin, delivers the desired salts in good yield and high purity.

Citations

• New Chiral Isoquinolinium Salt Derivatives from Chiral Primary Amines via Zincke Reaction
• Influence of para substituents on the rate of cyclization of 5-anilino-N-phenyl-2,4-pentadienylidenimine
• Formation of phenylpyridinium chloride from 5-anilino-N-phenyl-2,4-pentadienylideniminium chloride. Kinetics in basic media

Cited by

• Zincke reaction [wikipedia]