Art

J-GLOBAL ID：200902154062398980   Reference number：02A0165517

A Convenient Synthesis of 1,1-Disubstituted 1,2,3,4-Tetrahydroisoquinolines via Pictet-Spengler Reaction Using Titanium(IV) Isopropoxide and Acetic-Formic Anhydride.

チタニウム(IV)イソプロポキシド及び酢酸-ぎ酸無水物を用いるPictet-Spengler反応を経由する1,1-二置換1,2,3,4-テトラヒドロイソキノリン類の簡便合成

Author (8)： HORIGUCHI Y (Showa Pharmaceutical Univ., Tokyo, JPN) ,  KODAMA H (Showa Pharmaceutical Univ., Tokyo, JPN) ,  NAKAMURA M (Showa Pharmaceutical Univ., Tokyo, JPN) ,  YOSHIMURA T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  HANEZI K (Showa Pharmaceutical Univ., Tokyo, JPN) ,  HAMADA H (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SAITOH T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SANO T (Showa Pharmaceutical Univ., Tokyo, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 50  Issue： 2  Page： 253-257  Publication year： Feb. 01, 2002 
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 ,...
Semi thesaurus term： Pictet-Spengler reaction

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JST classification (1)： Quinolines,isoquinolines  (CF07096H)

Substance index (33)： Acetophenone ,  Acetone ,  Benzophenone ,  Cyclopentanone ,  Cyclohexanone ,  3,4-Dimethoxybenzeneethanamine ,  3-Methoxybenzeneethanamine ,  Methyl ethyl ketone ,  1-(Phenylthio)-2-propanone ,  Indan-1-one ,  Titanium(IV)tetraisopropoxide ,  1-Methyl-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1-Methyl-1-phenyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1,1-Dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1,1-Dimethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1-Methyl-1-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1-Methyl-1-(phenylthiomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  1,1-Diphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-cyclopentane]-2-carbaldehyde ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-cyclohexane]-2-carbaldehyde ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-indan]-2-carbaldehyde ,  1-Methyl-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  1-Methyl-1-phenyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline ,  1,1-Dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  1,1-Dimethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline ,  1-Ethyl-1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  1-Methyl-1-(phenylthiomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  1,1-Diphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-cyclopentane] ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-cyclohexane] ,  6,7-Dimethoxy-3,4-dihydrospiro[isoquinoline-1(2H),1′-indan] ,  N-(1-Phenylethenyl)-N-(3,4-dimethoxyphenethyl)formamide ,  N-(1-Phenylethyl)-3,4-dimethoxybenzeneethanamine

Reference (16)：

• LUNDSTROM, J. The Alkaloids. 1893, 21, 255-327
• COLLINS, M. A. The Alkaloids. 1893, 21, 329-358
• BROSSI, A. The Alkaloids. 1993, 43, 119-183
• NAGATSU, T. Neuroscience Res. 1997, 29, 99-111
• BRINGMANN, G. Comprehensive Organic Synthesis. 1991, 6, 736-739

Terms in the title (9)： チタニウム ,  イソプロポキシド ,  酢酸 ,  ぎ酸 ,  無水物 ,  Pictet-Spengler反応 ,  置換 ,  テトラヒドロイソキノリン類 ,  簡便