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1‐Acetamido‐17‐carbomethoxydihydrothebainone
Author(s) -
Archer Sydney,
Okaniwa Kenichiro,
Schepis Dominic J.,
Moharir Yadunath E.,
Klinowski Carl W.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180226
Subject(s) - chemistry , boron trifluoride , sulfanilic acid , medicinal chemistry , yield (engineering) , ammonia , ethanol , organic chemistry , potassium , hydrolysis , catalysis , materials science , metallurgy
Treatment 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.