Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Tetrahydroisoquinolines. XXXVII. : A Synthesis of 3-Hydroxyaporphines and 3-Hydroxyhomoaporphines
HIROSHI HARAHIROSHI SHINOKITOSHIYA KOMATSUOSAMU HOSHINOBUNSUKE UMEZAWA
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Keywords: cyclization
JOURNAL FREE ACCESS

1986 Volume 34 Issue 5 Pages 1924-1928

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Abstract
Acid treatment of o-quinol acetates (2a and 2b) derived from 5-hydroxy-1-benzyltetrahydroisoquinolines (3a and 3b) gave the corresponding 3-hydroxyaporphines (4a and 4b) in high yield.Similarly, the 3-hydroxyhomoaporphines (4c, 4d, and 4e) were excusively synthesized from the corresponding 1-phenethyl o-quinol acetates (2c, 2d, and 2e). On the other hand, no C-noraporphine was formed from the 1-aryl o-quinol acetate (2f); instead, the p-quinone (11) was generated.
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© The Pharmaceutical Society of Japan
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