Abstract

The first example of abnormal Michael reaction of an active methylene compound, 2-acylmethyl-4,4-dimethyl-2-oxazoline with acetylenic ketone in acetonitrile is reported. The reaction accompanies 1,3-migration of the acyl group of the substrate to give 2-(3-acyl-1-buten-4-on-1-yl)-2-oxazoline, which was easily cyclized to 5-acyl-2-pyridone derivatives by treatment with silica gel. Selectivity of the reaction depends on bulkiness of all the substituents of both the substrate and the reagent. The selectivity is interpreted in terms of reduced kinetic acidity of an initial anionic adduct intermediate by both steric and electronic factors.

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