128134-26-9Relevant academic research and scientific papers
BENZOPHENANTHRIDINES. XII. INVESTIGATION OF THE RODIONOV-SUVOROV SCHEME. SYNTHESIS OF DIETHYL 6-METHYL-2,3,8,9-TETRAMETHOXY-11,12-DIHYDROBENZOPHENANTHRIDINE-11,11-DICARBOXYLATE
Kyong, Dao Hung,Sladkov, V. I.,Suvorov, N. N.
, p. 167 - 172 (2007/10/02)
Diethyl 6-methyl-2,3,8,9-tetramethoxy-11,12-dihydrobenzophenanthridine-11,11-dicarboxylate was synthesized with a 41.3percent yield starting from the tricyclic Rodionov-Suvorov ACD synthon, i.e., diethyl 3-(3,4-dimethoxyphenyl)-4-tetralone-2,2-dicarboxylate, through stages involving oximation by methoxyamine hydrochloride in pyridine, reductive acetylation by zinc dust in a mixture of acetic acid and acetic anhydride, and Bischler-Napieralski cyclization by boiling with an excess of phosphorus oxychloride.An unusual Beckmann fragmentation, i.e., intramolecular alkylation of diethyl 4-methoxyimino-3-(3,4-dimethoxyphenyl)-6,7-dimethoxytetralin-2,2-dicarboxylate, was discovered.
