dl-4,4´-Bis(2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolylmethyl)biphenylおよびdl-5,5´-Bis-(2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl-methyl)-2,2´-dimethoxybiphenylの合成

抄録

Some model compounds of bis(benzyltetrahydroisoquinoline)-type bases with biphenyl structure in the molecule were synthesized. dl-4, 4′-Bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro-1-isoquinolylmethyl)biphenyl (XII) was synthesized by the route shown in Chart 1 from 3, 4-dimethoxyphenethylamine (VI) and 4, 4′-biphenyldiacetyl chloride (VII), through bis-acetamide (VIII) and bis-3, 4-dihydroisoquinoline (IX). Through the second route shown in Chart 2, 2, 2′-dimethoxybiphenyl (XIV) was derived to 2, 2′-dimethoxy-5, 5′-diacetylbiphenyl (XV) and then to 2, 2′-dimethoxybiphenyl-5, 5′-diacetic acid (XVII) by the Willgerodt-Kindler method, and further to bis-acetamide (XIX) and bis-3, 4-dihydroisoquinoline (XX) from (XVII) and 3, 4-dimethoxyphenethylamine (VI). (XX) was finally derived to the objective dl-5, 5′-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydrol-isoquinolylmethyl)-2, 2′-dimethoxybiphenyl (XXIII) via amino-1, 2, 3, 4-tetrahydroisoquinoline (XXI) or 3, 4-dihydroisoquinoline dimethiodide (XXII).
The ultraviolet spectra of (XII) and (XXIII) so obtained were examined comparatively with tiliacorine (III) assumed to possess biphenyl structure in its molecule and dauri-cine (XXIV) possessing diphenyl ether structure in its molecule.