Nucleophilic Reaction upon Electron-deficient Pyridone Derivatives. IV. Ring Transformation of 1-Substituted 3,5-Dinitro-2-pyridones with Ketones in the Presence of Amines

Article abstract of DOI:10.1246/bcsj.55.2174

Ring transformation of 1-substituted 3,5-dinitro-2-pyridones with 1,3-disubstituted acetones in the presence of secondary or primary amines gave p-nitroaniline derivatives and N-substituted 2-nitroacetamide.Two types of enamine intermediates, 2-azabicyclo<3.3.1>nonene derivatives and N-substituted 2-(5-amino-2-nitro-2,4-cyclohexadienyl)-2-nitroacetamides were isolated and characterized.The course of the base-catalyzed reaction is interpreted.