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Communication | Regular issue | Vol 14, No. 8, 1980, pp.1085-1088
Published online, 1st January, 1970
DOI: 10.3987/R-1980-08-1085
Synthesis of the 3,4,6,7-Tetrahydro-1H-1,5-methano-2,5-benzoxazonine Ring System by Cyanogen Bromide-Mediated Rearrangement of a 10b-Methyl-5H-oxazolo[2,3-a]isoquinoline Derivative

John B. Bremner* and Kevin N. Winzenberg

*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia


The new heterocyclic derivatives, 1,9,10-trimethoxy-3,4,6,7-tetrahydro-1H-1,5-methano-2,5-benzoxazonine (2a) and 9,10-dimethoxy-3,4,6,7- tetrahydro-1H-1,5-methano-2,5-benzoxazonine-1-carbonitrile (2b), were prepared in 76% and 4% yield respectively by the reaction of 8,9-dimethoxy-10b-methyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline (1b) with cyanogen bromide in the presence of methanol and potassium carbonate. Acid hydrolysis of (2a), followed by reduction with lithium tetrahydroaluminate, afforded 3-(2-hydroxy)ethyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol (4) in good yield. A mechanism of formation of (2a) and (2b) is outlined.