A benzyne reaction of 1-(2-bromo-4,5-methylenedioxybenzyl)-1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinoline (4) with sodium amide in liquid ammonia afforded amurine (10) and domesticine (13). The same reaction was carried out in the presence of potassium ferricyanide to give amurine (10) and 1,2,3,4-tetrahydro-7-hydroxy-1-(3-hydroxybenzyl)-6-methoxy-2-methylisoquinoline (6).
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Kametani et al. (1971) studied this question.
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