Issue 0, 1972

Reactive intermediates. Part XVIII. An N-aminopyridone-to-pyridazine rearrangement; a new decarbonylation reaction

Abstract

Oxidation of 1-amino-3,4,5,6-tetraphenyl-2-pyridone with lead tetra-acetate results in loss of carbon monoxide and retention of nitrogen to give 3,4,5,6-tetraphenylpyridazine. This rearrangement is thought to involve ring expansion of the N-nitrene to a diazepinone and valence tautomerism of this to give a bicyclic intermediate which extrudes carbon monoxide. This reaction can be suppressed by competitive intermolecular reaction of the nitrene with sulphoxides or with cyclohexene. This pyridone-to-pyridazine rearrangement is observed to a much smaller extent with di- and tri-phenyl-1-amino-2-pyridones, and not at all with 1-amino-2,3-diphenylquinolin-4-one or 5-aminophenanthridin-6-one.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 77-82

Reactive intermediates. Part XVIII. An N-aminopyridone-to-pyridazine rearrangement; a new decarbonylation reaction

C. W. Rees and M. Yelland, J. Chem. Soc., Perkin Trans. 1, 1972, 77 DOI: 10.1039/P19720000077

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements