The Stevens rearrangement of quarternary isoquinolinium salts.

Abstract

The reaction of 1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-1-(3, 4-methylenedioxyphenyl)-2, 2-dimethylisoquinolinium iodide (3) with dimsylsodium afforded the 1-methyl-1-phenylisoquinoline (4) and the N, N-dimethyldiphenylmethylamine (5). Similar reaction using the berbine methiodide (8), (16), (17) yielded the corresponding ochotensine type 1-spirobenzylisoquinolines (9), (14), and (15), respectively. The homoberbine (20) also gave the 1-spiroisoquinoline (22), however, the reaction of the homoberbine (23) with dimsylsodium yielded the tetrahydro-13, 14-trans-dibenz [c, g] azacycloundecine (28).