A. Schmidt, T. Mordhorst, M. Nieger
Feb 20, 2006
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0
Influential Citations
5
Citations
Journal
Tetrahedron
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 N 2 ,S 4 ,N 6 -, O 2 ,S 4 ,O 6 -, O 2 ,O 6 -, N 2 ,N 6 -, and S 2 ,S 6 -substitution patterns.