Benzyne reaction. Part XII. Syntheses of amurine and domesticine by the benzyne reaction

Abstract

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).