1-(3-および4-Chlorobenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolineの合成ならびにそのBenzyne反応成績体について : 複素環式化合物の合成研究 第241報

抄録

As 1-(4-chlorobenzyl)- (I) and 1-(4-chlorophenethyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2-methylisoquinoline (II) are reported to possess anesthetic activities, syntheses of 1-(4-chlorobenzyl)-(IXa) and 1-(3-chlorobenzyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxyisoquinoline (IXb) from 4-chloro-(VIa) and 3-chlorophenylacetic acid (VIb), and homoveratrylamine (V) through the corresponding amides (VIIa, (VIIa, and 3, 4-dihydroisoquinoline (VIIIa, VIIIb) expecting the similar effects to the resembling compounds. When (IXb) is treated with sodium amide in liquid ammonia, and purified in the dark, then 2, 3-dimtehoxy-5, 6-dihydrodibenzo [b, g] pyrrocoline (IV) is afforded. However, when it is purified through alumina chromatography with benzene, the dehydrogenated 2, 3-dimethoxy dibenzo [b, q] pyrrocoline (III) is obtained. In this reaction, it is clear that the benzyne is an intermediate, for the cine-substitution type of reaction is considered to be taken place.