Benzoylation of the sodium salt of 6(5H)-phenanthridinone and an O-to-N benzoyl migration

✍ Scribed by David Y. Curtin; John H. Engelmann

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 170 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72365-3

✦ Synopsis

In our-study of 1,3 acyl migrations (1,2) heterocycles are of particular interest because of their freedom from complications due to E-anti isomerism. We were struck by the scarcity of pairs of isomeric N-and 0-acyl derivatives in simple aromatic heterocyclic systems such as the ocpyridones and the pyrimidones (3). Preliminary work was carried out on the acylation of the sodium salt of 2-pyridone in benzene. Spectral evidence (4) that mixtures of N-and 0-acyl products were being formed led us to shift to a study of the reaction of benzoyl chloride at -200 with the sodium salt (3) of 6-phenanthridinone, prepared from reaction of 6-phenanthridinone in tetrahydrofuran with sodium hydride. Removal of the solvent without heating gave the G-benzo-