75288-89-0Relevant academic research and scientific papers
Benzolactams. II. Synthesis of Tetrahydrobenzindenoazepines and their 12-Oxo Derivatives
Orito, Kazuhiko,Kaga, Harumi,Itoh, Mitsuomi,Silva, S. Osmund de,Manske, Richard H.,Russel, Rodrigo
, p. 417 - 423 (2007/10/02)
Aromatic methoxy and/or methylenedioxy substituted 7-methyltetrahydrobenzindenoazepines 7 and their 12-oxo derivatives 8 were efficiently synthesized by the general method consisting of two types of intramolecular dehydrative cyclizations, as follows.N-Methyl-N-β-phenethylacetamides 1 were cyanomethylated in the two-step process of chloromethylation and treatment of the resultant benzyl chlorides with sodium cyanide.The condensation of the benzyl cyanides 2 with the appropriate benzaldehydes, followed by reduction of the benzylidene function, gave α,β-diphenylpropionitriles 3.Successively, hydrolysis to the amino acids 4 and the thermal cyclization converted 3 to the benzylbenzazepinones 5, which were also prepared by benzylation of the benzazepinones 6 smoothly by heating of 5 with phosphoryl chloride to afford the title azepines 7.Further, these tetracyclic enamines 7 underwent autoxidation to the corresponding 12-oxo derivatives 8, on exposure to oxygen in the presence of Triton B.
