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

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

Volume: 3 Issue: 8

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

Affiliation:

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

Abstract: 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.

Cite this article as:

Nishiwaki Nagatoshi, Tatsumichi Hiroshi, Tamura Mina and Ariga Masahiro, Three Components Ring Transformation Affording Substituted 5-Nitropyridines and 4-Nitroanilines, Letters in Organic Chemistry 2006; 3 (8) . https://dx.doi.org/10.2174/157017806778559563