The Reaction of α-Oxo Acids with <I>N</I>-Phenyltriphenylphosphinimine

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概要

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• The reaction between ethyl α-oxocarboxylate and <I>N</I>-phenyltriphenylphosphinimine gave a mixture of ethyl α-phenyliminocarboxylate (IVa–f) and the tautomeric isomers (Va–f) in good yield. IVa and Va derived from ethyl pyruvate was converted gradually into 3-anilino-5-ethoxycarbonyl-5-methyl-1-phenyl-<I>Δ</I><SUP>3</SUP>-pyrrolin-2-one (VIIa) on standing at room temperature. The free acid of IVa and Va prepared by the same method could not be purified, but a small amount of 3-anilino-5-methyl-l-phenyl-<I>Δ</I><SUP>3</SUP>-pyrrolin-2-one (IX) was obtained from the reaction mixtures. In the reaction of aniline and pyruvic acid, α,γ-dianilino-γ-carboxy-α-methyl-γ-butyrolactone (XII) was obtained in the neutral reaction condition and 4-anilino-2-phenyliminopentanoic acid (XIV) in basic condition. The structure of the products was proved by NMR and IR spectrum, and the reaction courses were discussed.

• 公益社団法人 日本化学会の論文

著者

• Shin Chung-gi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

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