Synthesis of 2-Aryl-5-Nitropyridines by Three-Component Ring Transformation of 3,5-Dinitro-2-Pyridone

2-Arylated-5-nitropyridines were efficiently synthesized by a three-component ring transformation of 3,5-dinitro-2-pyridone with aromatic ketones in the presence of ammonium acetate, in which the dinitropyridone serves as a synthetic equivalent of an unstable nitromalonaldehyde. Although a 2,8-diazabicyclo[3.3.1]non-3-ene derivative was also formed as a byproduct, it was converted into nitropyridines under the reaction conditions, heating in the presence of ammonium acetate. This experimental fact implies that the former compound is a kinetically controlled product and the latter is a thermodynamically controlled product because of the aromatization. This method is applicable to various kinds of aryl and (hetero)aryl ketones to afford the corresponding (hetero)arylated pyridines in good to excellent yields

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