Syntheses of dibenzo(b,f)azonines and dibenzo(b,g)azecines through ring expansion of 1-substituted isoquinolines.

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The reaction of 1-(2-bromo-4, 5-methylenedioxyphenethyl)-1, 2, 3, 4-tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinoline (13) with sodium methylsulfinylmethanide gave the dibenzo [b, g] azecine (14). The 1-benzyl analog possessing a methyl group at the 3-position was transformed to the 6, 13-disubstituted dibenzo [b, f] azonine (33) under the similar conditions. 33 was converted to the corresponding 6, 13-dimethyl derivative (35). Hydrogenolysis of the N-methyl-dibenzo [a, f] quinolizinium iodide (23) over Adams catalyst was also examined to give the dibenzo [b, g] azecine (24).

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