Three Components Ring Transformation Affording Substituted 5-Nitropyridines and 4-Nitroanilines

Author(s): Nagatoshi Nishiwaki, Hiroshi Tatsumichi, Mina Tamura, Masahiro Ariga.

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 8 , 2006

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The ring transformation of 1-methyl-3,5-dinitro-2-pyridone afforded 2-aryl-5-nitropyridines upon treatment with aromatic ketones in the presence of ammonium acetate. In reactions with aliphatic ketones, 2,6- disubstituted 4-nitroanilines could be prepared in addition to corresponding 2,3-disubstituted 5-nitropyridines. In these reactions, dinitropyridone behaved as the synthetic equivalent of unstable nitromalonaldehyde.

Keywords: Ring transformation, dinitropyridone, nitropyridine, nitroaniline, bicyclic intermediate, nitromalonaldehyde

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Article Details

Year: 2006
Page: [629 - 633]
Pages: 5
DOI: 10.2174/157017806778559563
Price: $58