Rearrangement in the Series of Acetyltetrahydropyridine Derivatives

Abstract

Michael addition of various substituted benzylidene- and thiophen-2-ylmethylidenemalononitriles with acetoacetanilide gave the corresponding 5-acetyl-2-amino-4-aryl(hetaryl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitriles. Treatment of the latter with ethylenediamine in boiling methanol resulted in their rearrangement with elimination of the acetyl group and formation of 2-anilino-4-aryl(hetaryl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles. The product structure was proved by NMR spectroscopy and X-ray analysis.