Studies on Tetrahydroisoquinolines. XXIX. Reaction of 7-Acetoxy-1, 2, 3, 4, 6, 7-hexahydro-1- (2- (3', 4'-dimethoxy-or 3', 4'-methylenedioxyphenyl) ethyl) -7-methoxy-2-methyl-6-oxo-isoquinoline (o-Quinol Acetate) with Acetic Anhydride in the Presence of Acid

OSAMU HOSHINO; KYOKO KIKUCHI; HIDETO OGOSE; BUNSUKE UMEZAWA; OICHI IITAKA

doi:10.1248/cpb.35.3666

OSAMU HOSHINO, KYOKO KIKUCHI, HIDETO OGOSE, BUNSUKE UMEZAWA, OICHI IITAKA

著者情報

キーワード: lead tetraacetate oxidation, X-ray analysis, o-quinol acetate, 1, 2, 3, 4-tetrahydro-1-phenethylisoquinolin-6-ol, aldehyde-amide, 2-acetoxyhomoaporphine, acetic anhydride, concentrated sulfuric acid, boron trifluoride etherate, trifluoroacetic acid

ジャーナルフリー

1987 年 35 巻 9 号 p. 3666-3675

DOI https://doi.org/10.1248/cpb.35.3666

詳細

抄録

Treatment of o-quinol acetates (5a, b) of 1, 2, 3, 4-tetrahydro-1-phenethylisoquinolin-6-ols (6a, b) with acetic anhydride in the presence of an acid (concentrated H₂SO₄, BF₃ · Et₂O or CF₃COOH) gave 2-acetoxyhomoaporphines (4a, b) and/or aldehyde-amides (7a, b), and the ratio of the products was strongly dependent on the choice of the acid and the solvent. A mechanistic pathway is proposed.

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