Studies on the synthesis of heterocyclic compounds CDLXXXIII. Synthesis of homoaporphines and attempts to synthesize C-noraporphines by Pschorr reaction

Abstract

Photolysis of the diazonium salt derived from l-(2-amino-4-hydroxy-5-methoxy-phenethyl)-7-hydrox}'-l;2,3,4-tetrahydro-6-methoxy-2-methylisoquinoline (V) gave, 1,11-dihydroxy-2,10-dimethoxyhomoaporphine (IX), which was identical with the rearranged product of kreysiginone (VII) by acid. The same reaction of l-(2-aminophenyl)-l,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline (XXI) gave an abnormal product, 3,4-dihydro-6,7-dimethoxy-l-phenylisoquino]ine (XXV), in addition to the deamination product (XXII) and the phenolic isoquinoline (XXIII).