The solid-phase zincke reaction: Preparation of ω-hydroxy pyridinium salts in the search for CFTR activation

Masahiro Eda, Mark J. Kurth, Michael H. Nantz

Research output: Contribution to journalArticle

29 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)5131-5135
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number17
DOIs
StatePublished - Aug 25 2000

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Salts
Chemical activation
Ethers
Ammonium Compounds
Amines
Polymers
Resins
Derivatives
Molecules
6-hydroxy-10-chlorobenzo(c)quinolizinium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

The solid-phase zincke reaction : Preparation of ω-hydroxy pyridinium salts in the search for CFTR activation. / Eda, Masahiro; Kurth, Mark J.; Nantz, Michael H.

In: Journal of Organic Chemistry, Vol. 65, No. 17, 25.08.2000, p. 5131-5135.

Research output: Contribution to journalArticle

Eda, Masahiro ; Kurth, Mark J. ; Nantz, Michael H. / The solid-phase zincke reaction : Preparation of ω-hydroxy pyridinium salts in the search for CFTR activation. In: Journal of Organic Chemistry. 2000 ; Vol. 65, No. 17. pp. 5131-5135.
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