Lithiation of 1-methyl-4-pyridone with n-butyl-lithium at -78 °C proceeds smoothly at the C-2 position and 2-substituted-4-pyridones (1c–j) are obtained by subsequent reaction with electorphiles; lithiation of 1-methyl-2-pyridone takes place predominantly at the N-methyl, the lithio-derivative reacting rapidly, even at -78 °C with starting pyridone to give a dimer, (3).
P. Patel and J. A. Joule, J. Chem. Soc., Chem. Commun., 1985, 1021 DOI: 10.1039/C39850001021
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