Reaction of α, β-Unsaturated Ketones with Compounds containing an Active Methylene Group. A Synthesis of (3H)-1, 2-Diazepin-3-one Derivatives

Abstract

1, 3-Diaryl-2-propen-1-ones (IIa, b) reacted with methyl α-naphthylacetate (Ib) in the presence of sodium methoxide at room temperature, or under reflux to give only the corresponding 4, 6-diaryl-3-[3^^-(1^^-3^^-diarylpropan-1^^-one)]-3-α-naphthyl-4-hydro-2H-pyran-2-ones (IIIa, b). However, on reacting the ketones (IIc-f) with ethyl phenylacetate (Ia) in the presence of sodium ethoxide at room temperature, or under reflux, the corresponding ethyl γ-aroyl-β-aryl-α-phenyl-butyrates (IVa-d) or 4, 6-diaryl-3-[3^^-(1^^-, 3^^-diarylpropan-1^^-one)]-3-phenyl-4-hydro-2H-pyran-2-ones (IIIc, d), respectively, were obtained. The reaction of these compounds, (III) and (IV), with hydrazine hydrate gave the corresponding (3H)-1, 2-diazepin-3-one (VI) and hydrazone (IX) derivatives, respectively. The structures of the products were established by chemical and spectroscopic evidence.