K. Orito*, H. Kaga, M. Itoh
May 1, 1980
Citations
0
Influential Citations
6
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Aromatic methoxy and/or methylenedioxy substituted 7-methyltetrahydrobenz[d]indeno[1,2-b]-azepines 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.