Heterocycles. Part V. Reaction of α,β‐unsaturated carbonyl compounds with arylacetamides. A synthesis of 2‐pyridone derivatives

Abstract

AbstractThe reaction of 1,3‐diaryl‐2‐propene‐1‐ones I with arylacetamides II, in the presence of sodium ethoxide under reflux, for two hours, gave the corresponding 3,4,6‐triaryl‐3,4‐dihydro‐2(1H)‐pyridones IV. However, when the reaction of these ketones was carried out in the presence of sodium hydride, they gave the corresponding 3,4,6‐triaryl‐2(1H)‐pyridones VI or a mixture of IV and VI. When 1,3‐diaryl‐2‐propyne‐1‐ones V were reacted with arylacetamides, in the presence of sodium hydride, they yielded the corresponding 2‐pyridones VI. Treatment of compounds IV with selenium produced the corresponding 2‐pyridones VI. Acetylation of the latter compounds gave the corresponding 2‐acetyl derivatives VIII. The structure of all products was confirmed by chemical and spectroscopic evidence, and the mechanism of the reactions was discussed.