105166-32-3Relevant academic research and scientific papers
Bridged-ring Nitrogen Compounds. Part 7. Synthesis of the 1,4-Ethano-3-benzazepine Ring System
Sedgeworth, Janette,Proctor, George R.
, p. 2677 - 2688 (2007/10/02)
9-Bromobenzosuberone was converted via 9-cyanobenzosuberone into several other 9-substituted benzosuberones, but attemps to cause them to cyclise to the tricyclic 1,4-ethano-3-benzazepine ring system were unsuccessful.Both ethyl phenylacetate and ethyl 3-methoxyphenylacetate were converted by conventional procedures into the corresponding 6,7,8,9-tetrahydro-5-methyl-9,10-dioxo-5,8-methano-5H-benzocycloheptenes.The 3-methoxy derivative was further converted into N-benzyl-8-bromo-6,7,8,9-tertrahydro-3-methoxy-5-methyl-9-oxo-5H-benzocycloheptene-5-carboxamide which could be converted into the tricyclic 3-benzyl-2,3,4,5-tetrahydro-8-methoxy-1-methyl-2,5-dioxo-1,4-ethano-1H-3-benzazepine and thence in two steps into both 3-benzyl-2,3,4,5-tetrahydro-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepine and 3-benzyl-2,3,4,5-tetrahydro-8-hydroxy-1-methyl-1,4-ethano-1H-3-benzazepine.Also prepared were 3-benzyl-2,3,4,5-tetrahydro-5-hydroxy-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepine and 3-benzyl-3,4-dihydro-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepin-5(2H)-one.
