Selective functionalization at the α‐methyl group of 1‐substituted pyridin‐2(1H)‐ and 4(1H)‐ones (2‐ and 4‐pyridones) can be achieved by appropriate choice of base. n‐Butyllithium was found to effect clean 6(2)‐methyl deprotonation of 1‐benzyl‐2‐ and ‐4‐pyridone derivatives, while potassium hexamethyldisilazide (KHMDS) was the preferred reagent for methyl deprotonation of the corresponding 1‐methyl‐2‐ and ‐4‐pyridones. Deprotonation proceeds smoothly at –78 °C, and the resulting anions react readily with a wide range of electrophiles (aldehydes, ketones, alkylating reagents, and an azo compound) under precise temperature control to form usefully functionalized 2‐ and 4‐pyridones and quinolizinones.
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