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Communication | Regular issue | Vol 16, No. 6, 1981, pp.885-887
Published online, 1st January, 1970
DOI: 10.3987/R-1981-06-0885
Reaction of Cyanogen Bromide with 1-(ω-Hydroxyalkyl)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizines as a Route to Annelated Benzazecine Derivatives

John B. Bremner* and Narumol Thirasasana

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


Treatment of 1-(2-hydroxyethyl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine (4a) with cyanogen bromide in chloroform/potassium carbonate gave the new heterocyclic product, 11,12-dimethoxy-2,3,3a,5,6,8,9,13b-octahydro-furo[3,2-g][3]benzazecine-7(4H)-carbonitrile (5a) in moderate yield. The corresponding octahydro-2H-pyrano[3,2-g]- and decahydrooxepino[3,2-g]-benzazecine-carbonitrile derivatives (5a and 5c) were prepared similarly from the appropriate reduced 1-(ω-hydroxyalkyl)-2H-benzo[a]quinolizines. Elimination products were also isolated in some cases.