Synthesis of Alkoxy-Substituted Pyridines from Mono- and Tricationic Pyridinium Salts

Andreas Schmidt; Thorsten Mordhorst

doi:10.1055/s-2005-861827

PAPER

Synthesis of Alkoxy-Substituted Pyridines from Mono- and Tricationic Pyridinium Salts

Andreas Schmidt*, Thorsten Mordhorst
Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)723861; e-Mail: schmidt@ioc.tu-clausthal.de;

Abstract

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Abstract

Nucleophilic substitution reactions on 4-(4-dimethylamino)-pyridinium-substituted tetrachloropyridine with oxygen nucleophiles such as alkoxides and phenolates resulted in the formation of 4- or 2,4-alkoxy- or -phenoxy-substituted chloropyridines depending on the reaction conditions. Substitution on 2,4,6-tris(4-dimethylamino)pyridinium-substituted 3,5-dichloropyridine gave the corresponding 2,4,6-tris-alkoxy- or -phenoxy-substituted pyridines which are not available by other routes.

Key words

nucleophilic aromatic substitutions - pyridinium salts - pyridines - trication

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