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Free‐Radical Approach to 4‐Substituted Dipicolinates
Author(s) -
Shelkov Rimma,
Melman Artem
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400637
Subject(s) - chemistry , radical , pyridine , hydrogen atom abstraction , radical substitution , protonation , alkyl , medicinal chemistry , free radical reaction , beta scission , organic chemistry , ion
Dimethyl pyridine‐2,6‐dicarboxylate was selectively substituted through free‐radical reactions. The substitution involves the generation of free radicals through Fenton‐type reactions, followed by hydrogen abstraction from aldehydes or alcohols. The resultant carbon‐centered acyl, alkyl, or hydroxyalkyl free radicals regioselectively attack protonated dimethyl pyridine‐2,6‐dicarboxylate at position 4, yielding the corresponding dimethyl 4‐acyl‐, 4‐alkyl‐, and 4‐(hydroxyalkyl)pyridine‐2,6‐dicarboxylates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)