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Functionalization of substituted 2(1 H )‐pyridones. V. The synthesis of 1,2‐dihydro‐2‐oxo‐3,5‐pyridinedicarboxylic acid derivatives through a novel dianion route
Author(s) -
Domagala John M.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210626
Subject(s) - chemistry , electrophile , amide , pyridine , halogen , hydrolysis , butyllithium , medicinal chemistry , surface modification , ethyl ester , organic chemistry , catalysis , alkyl
A new pyridone dianion was prepared by halogen‐metal exchange from 5‐bromo‐1,2‐dihydro‐2‐oxo‐3‐pyrid‐inecarboxylic acid, t ‐butyl ester and two equivalents of n ‐butyllithium. This 1,5‐dianion readily reacted at C 5 with electrophiles. Quenching with carbon dioxide gave the previously unreported 1,2‐dihydro‐2‐oxo‐3,5‐pyridine dicarboxylic acid, 3‐ t ‐butyl ester. The 5‐carboxyl groups were selectively converted to the ethyl ester and the ethyl amide through the 5‐imidazolide. The 3‐ t ‐butyl ester was easily removed from all derivatives with acid hydrolysis.