Heteroarenium salts in synthesis. Highly functionalized tetra- and pentasubstituted pyridines |
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| Authors: | Andreas Schmidt Thorsten Mordhorst |
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| Institution: | a Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany
b Rheinische Friedrich-Wilhelms-Universität Bonn, Institute of Inorganic Chemistry, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany |
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| Abstract: | Activation of chloropyridines by heteroarenium substituents allows sequential substitutions by O-, N-, and S-nucleophiles. Reaction of 2,3,5,6-tetrachloropyridine and 4-ethylsulfanyl-2,3,5,6-tetrachloropyridine with 4-(dimethylamino)pyridine, 4-(pyrrolidin-1-yl)pyridine, or 4-aminopyridine results in the formation of 2,6-bis-heteroarenium substituted 3,5-dichloropyridines. On nucleophilic displacement of the heteroarenium substituents by O-, N-, or S-nucleophiles highly functionalized 3,5-dichloropyridines form which possess N2,S4,N6-, O2,S4,O6-, O2,O6-, N2,N6-, and S2,S6-substitution patterns. |
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| Keywords: | Heteroarenium Pyridines Nucleophiles |
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