複素環式化合物の合成研究(第442報) : Streptonigrin関連化合物の合成研究(第10報) : Methyl 3-Acetamido-1,2-dihydro-4-(2,3,4-trimethoxyphenyl)-5-methyl-2-oxo-6-pyridinecarboxylateの合成

概要

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Michael cyclization of keto ester (VII), which was obtained by condensation of 2,3,4-trimethoxybenzaldehyde (V) and ethyl 2-oxobutyrate (VI), with cyanoacetamide afforded a pyridone derivative (IX), which was further methylated with diazomethane to an unexpected mixture of X and XI. Esterification of IX with methyl iodide in the presence of sodium hydrogen carbonate gave the expected compound (XII). Futhermore, condensation of VII with aceturic amide gave dihydropyridone (XVI), which was methylated to afford an ester (XVII). Dehydrogenation of XVII with palladium-black afforded a hydrogenated compound (XVIII). The same reaction of XVII with platinum oxide gave methyl 3-acetamido-1,2-dihydro-4-(2,3,4-trimethoxyphenyl)-5-methyl-2-oxo-6-pyridinecarboxylate (XIX).
社団法人日本薬学会の論文
1971-10-25