Abstract
AbstractTreatment of 1‐(5′‐benzyloxy‐4′‐methoxy‐2′‐nitrobenzyl)‐3,4‐dihydroisoquinoline 2 with lithium/ammonia followed by the addition of ethanol gave a mixture of the dibenz[b,g]indolizines 3 and 4. Omission of ethanol resulted in the formation of 3 only. The dihydroisoquinoline from 3,4‐dimethoxyphenylethyl amine behaved similarly.Reduction of 2a with sodium/ammonia resulted in cleavage to give the nitro‐guaiacol 8. Oxidation of 2a in the presence of potassium t‐butoxide gave a complex mixture from which the benzoyldihydroisoquinoline 5 and 2‐benzyloxy‐5‐nitroanisole were isolated in low yield.Treatment of the hexahydrobenzylisoquinoline 10 with diazotized sulfanilic acid, followed by reduction and then acetylation gave a diacetyl compound 12 which was hydrolyzed to 13. Ring closure with boron trifluoride gave the dihydrothebainone 14.
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