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 …

…, M Ariga, T Kawashima, K Tani, H Watanabe…

Index: Tohda; Eiraku; Nakagawa; Usami; Ariga; Kawashima; Tani; Watanabe; Mori Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 10 p. 2820 - 2827

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Citation Number: 44

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 ...