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Nucleophilic Reaction upon Electron-Deficient Pyridone Derivatives. X.One-Pot Synthesis of 3-Nitropyridines by Ring Transformation of 1-Methyl-3,5-dinitro-2-pyridone with Ketones or Aldehydes in the Presence of Ammonia

1990; Oxford University Press; Volume: 63; Issue: 10 Linguagem: Inglês

10.1246/bcsj.63.2820

1348-0634

Yasuo Tohda, Miyuki Eiraku, Takao Nakagawa, Yumi Usami, Masahiro Ariga, Toshihide Kawashima, Keita Tani, H. Watanabe, Yutaka Mori,

Synthesis and Biological Evaluation

Abstract The reaction of 1-methyl-3,5-dinitro-2-pyridone (1a) with ketones or aldehydes in the presence of ammonia gave alkyl- and/or aryl-substituted 3-nitropyridines (6) in moderate to high yields. Enamines derived from the ketones gave better results than did the ketones themselves; on the other hand, those derived from the aldehydes gave no 6 at all. On the basis of deuterium-labeled experiments, a mechanism comprising competitive ring transformations of 1a is proposed.