Diazotization of 6 '-aminopapaverine (5) in dilute sulfuric acid, followed by treatment with copper, gave the indazole 7 as the major product; the oxoaporphine 8, derived from the normal Pschorr product 9, was the minor product. In contrast, diazotization of 5 in 46% sulfuric acid, followed by Pschorr cyclization, gave papaverine (10, 4.3%), the 1-oxoaporphine 12 (2.4%), and the indenoisoquinoline 11 (30%). Acid treatment of 11 affords 12 almost quantitatively. Chemical conversions of 11 and 12 to the known aporphine bases glaucine (1) and thaliporphine (18), respectively, are described.
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