Nucleophilic reaction of electron-deficient pyridone derivatives. II. Ring transformation of 1-substituted 3,5-dinitro-4-pyridones with sodio .BETA.-keto esters.
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The reactions of 1-substituted 3,5-dinitro-4-pyridones [1-substituents: methyl (<B>1a</B>), 2-pyridyl (<B>1b</B>), 6-methyl-2-pyridyl (<B>1c</B>), and 4-pyridyl (<B>1d</B>)] with diethyl sodio-3-oxopentanedioate give 1-substituted 3,5-bis(ethoxycarbonyl)-4-pyridones and sodio-1,3-dinitro-2-propane. On the other hand, the reactions of the 4-pyridones (<B>1b</B>, <B>1c</B>, and <B>1d</B>) with ethyl sodioacetoacetate give ethyl 4-hydroxy-3,5-dinitrobenzoate together with aminopyridine homologues, and that of la gives furo [3,2-<I>b</I>] pyridine derivative. On the basis of the concept of soft and hard acids and bases, a stepwise nucleophilic attack of the anion of β-keto esters at the electrophilic center of the 2 and 6-positions or 2 and 3-positions of the 4-pyridones is proposed to interpret the variations of the reaction courses.
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