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.

• HOSHINO OSAMU

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• KIKUCHI KYOKO

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• OGOSE HIDETO

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• UMEZAWA BUNSUKE

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• IITAKA OICHI

  Faculty of Pharmaceutical Sciences, University of Tokyo

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.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 35 (9), 3666-3675, 1987

  公益社団法人 日本薬学会

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

詳細情報

• CRID: 1390282679144527232
• NII論文ID: 130003771079
• DOI: 10.1248/cpb.35.3666
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/35/9/35_9_3666/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可