Journal of Heterocyclic Chemistry p. 1295 - 1302 (1983)
Update date:2022-08-03
Topics:
DeJohn
Domagala
Kaltenbronn
Krolls
The synthesis of various substituted 6-vinyl-1,2-dihydro-2-oxo-3-pyridinecarboxylic acids from the dianions of 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile and the corresponding 3-t-butyl ester is reported. The dianions were generated with LDA in THF at low temperature and reacted with various carbonyl substrates. Several conditions for the dehydration and hydrolysis of these adducts to the vinyl pyridone acids are discussed. Employing the conditions used for the 2-pyridone analogs, a series of substituted 6-vinyl-1,4-dihydro-4-oxo-3-pyridinecarboxylic acids was prepared through the new dianion of 1,4-dihydro-6-methyl-4-oxo-3-pyridinecarboxylic acid, t-butyl ester.
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Doi:10.1021/ja00361a062
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