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α-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or α-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O -attack of the nitronate, which results in isoxazoline N -oxide. This protocol was applicable to 1,3-dicarbonyl compounds to afford dihydrofuran derivatives, including those derived from direct substitution of a nitro group caused by O -attack of enolate. It was found the reactivity was lowered by an electron-withdrawing group on the carbonyl moiety. When α-nitroketone was employed as a substrate, three kinds of products were possibly formed; of these, only isoxazoline N -oxide was identified. This result indicates that the substituting ability of nitronate is higher than that of enolate for the direct S N 2 substitution of a nitro group.

Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group