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Paper | Regular issue | Vol 48, No. 1, 1998, pp.53-59
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7986
Synthesis of 7,12-Dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-Dibenzylphenacylamines

Necdet Coskun* and Levent Büyükuysal

*Uludag University, Department of Chemistry, 16059-Bursa, Turkey


N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cyclization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-Dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid at room temperature.