Art

J-GLOBAL ID：200902157448349193   Reference number：01A0714666

A Synthesis of 3-Phenyl-1,2,3,4-tetrahydroisoquinoline and 2-Phenyl-1,2,4,5-tetrahydro-3H-3-benzazepine via Pummerer-Type Cyclization: Enhancing Effect of Boron Trifluoride Diethyl Etherate on the Cyclization.

Pummerer型環化反応を経由する3-フェニル-1,2,3,4-イソキノリン及び2-フェニル-1,2,4,5-テトラヒドロ-3H-3-ベンゾアゼビンの合成 環化反応における三ふっ化ほう素ジエチルエーテラートの促進効果

Author (5)： SAITOH T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  ICHIKAWA T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  HORIGUCHI Y (Showa Pharmaceutical Univ., Tokyo, JPN) ,  TODA J (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SANO T (Showa Pharmaceutical Univ., Tokyo, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 49  Issue： 8  Page： 979-984  Publication year： Aug. 01, 2001 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *nitrogen heterocyclic compound ,...

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JST classification (2)： Seven-membered heterocyclic compounds  (CF07110I) ,  Cyclization reaction,ring-opening reaction  (CF02050I)

Substance index (32)： 3,4-Dimethoxybenzylamine ,  3,4-Dimethoxybenzeneethanamine ,  N-[1-Phenyl-2-(phenylthio)ethyl]-3,4-dimethoxybenzenemethanamine ,  N-[1-Phenyl-2-(phenylthio)ethyl]-3,4-dimethoxybenzeneethanamine ,  N-(3,4-Dimethoxybenzyl)-N-[1-phenyl-2-(phenylthio)ethyl]formamide ,  N-(3,4-Dimethoxyphenethyl)-N-[1-phenyl-2-(phenylthio)ethyl]formamide ,  N-(3,4-Dimethoxybenzyl)-N-[1-phenyl-2-(phenylsulfinyl)ethyl]formamide ,  N-(3,4-Dimethoxyphenethyl)-N-[1-phenyl-2-(phenylsulfinyl)ethyl]formamide ,  (3R)-3α-Phenyl-4β-(phenylthio)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (3R)-3α-Phenyl-4α-(phenylthio)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (3S)-1α-(Phenylthio)-2β-phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carbaldehyde ,  (3R)-1β-(Phenylthio)-2β-phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carbaldehyde ,  2-Phenyl-7,8-dimethoxy-4,5-dihydro-3H-3-benzazepine-3-carbaldehyde ,  N-(3,4-Dimethoxybenzyl)-N-[1-phenyl-2-(phenylthio)ethenyl]formamide ,  N-(3,4-Dimethoxyphenethyl)-N-[1-phenyl-2-(phenylthio)ethenyl]formamide ,  N-(3,4-Dimethoxybenzyl)-N-[2-(phenylsulfinyl)ethenyl]formamide ,  4-(Phenylthio)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  3-Phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  2-Phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carbaldehyde ,  3-Phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  2-Methyl-3-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  2-Phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine ,  2-Phenyl-3-methyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine ,  1-Phenyl-1-(phenylthiomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1-Methyl-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1-Methyl-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  1-Phenyl-1,2-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  [Phenyl[[2-[formyl(3,4-dimethoxybenzyl)amino]-2-phenylethane-1-ylium]-1-yl]sulfonio]trifluoroboronanion ,  [Phenyl[[2-[formyl(3,4-dimethoxyphenethyl)amino]-2-phenylethane-1-ylium]-1-yl]sulfonio]trifluoroboronanion ,  α-(Phenylthio)acetophenone ,  N-[1-Phenyl-2-(phenylthio)ethylidene]-3,4-dimethoxybenzenemethanamine ,  N-[1-Phenyl-2-(phenylthio)ethylidene]-3,4-dimethoxybenzeneethanamine

Reference (23)：

• 1) a) Shinohara T., Toda J., Sano T., Chem. Pharm. Bull., 45, 813-819 (1997)
•  b) Shinohara T., Takeda A., Toda J., Terasawa N., Sano T., Heterocycles, 46, 555-565 (1997)
•  c) Shinohara T., Takeda A., Toda J., Ueda Y., Kohno M., Sano T. Chem. Pharm. Bull., 46, 918-927 (1998)
•  d) Shinohara T., Takeda A., Toda J., Sano T., ibid., 46, 430-433 (1998)
•  e) Toda J., Matsumoto S., Saitoh T., Sano T., ibid., 48, 91-98 (2000).

Terms in the title (5)： 環化反応 ,  フェニル ,  イソキノリン ,  三ふっ化ほう素 ,  促進