Art

J-GLOBAL ID：200902270189489705   Reference number：03A0386627

Super Acid-Induced Pummerer-Type Cyclization Reaction: Improvement in the Synthesis of Chiral 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinolines

超酸誘発Pummerer型環化反応:キラルな1,3-ジメチル-1,2,3,4-テトラヒドロイソキノリン類の合成における改良

Author (4)： SAITOH T (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SHIKIYA K (Showa Pharmaceutical Univ., Tokyo, JPN) ,  HORIGUCHI Y (Showa Pharmaceutical Univ., Tokyo, JPN) ,  SANO T (Showa Pharmaceutical Univ., Tokyo, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 51  Issue： 6  Page： 667-672  Publication year： Jun. 01, 2003 
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)： Quinolines,isoquinolines  (CF07096H) ,  Cyclization reaction,ring-opening reaction  (CF02050I)

Substance index (24)： 1β,3α-Dimethyl-1,2,3,4-tetrahydroisoquinoline ,  1α,3β-Dimethyl-1,2,3,4-tetrahydroisoquinoline ,  1β,3β-Dimethyl-1,2,3,4-tetrahydroisoquinoline ,  1α,3α-Dimethyl-1,2,3,4-tetrahydroisoquinoline ,  (R)-1-Phenylethanamine ,  (S)-1-Phenylethanamine ,  (2R)-N-[(R)-1-Phenylethyl]-1-(phenylthio)-2-propanamine ,  (2S)-N-[(R)-1-Phenylethyl]-1-(phenylthio)-2-propanamine ,  (2S)-N-[(S)-1-Phenylethyl]-1-(phenylthio)-2-propanamine ,  (2R)-N-[(S)-1-Phenylethyl]-1-(phenylthio)-2-propanamine ,  N-[(R)-α-Methylbenzyl]-N-[(R)-1-methyl-2-phenylsulfinylethyl]formamide ,  N-[(R)-α-Methylbenzyl]-N-[(S)-1-methyl-2-phenylsulfinylethyl]formamide ,  N-[(S)-α-Methylbenzyl]-N-[(S)-1-methyl-2-phenylsulfinylethyl]formamide ,  N-[(S)-α-Methylbenzyl]-N-[(R)-1-methyl-2-phenylsulfinylethyl]formamide ,  (1R)-1β,3α-Dimethyl-4α-(phenylthio)-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (1R)-1β,3α-Dimethyl-4β-(phenylthio)-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (1R)-1β,3α-Dimethyl-4β-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (1R,3R)-1,3-Dimethyl-3,4-dihydroisoquinoline-2(1H)-carbaldehyde ,  (1R)-1β,3α-Dimethyl-4α-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde ,  (1S,3S)-1,3-Dimethyl-3,4-dihydroisoquinoline-2(1H)-carbaldehyde ,  (1R,3S)-1,3-Dimethyl-3,4-dihydroisoquinoline-2(1H)-carbaldehyde ,  (1S,3R)-1,3-Dimethyl-3,4-dihydroisoquinoline-2(1H)-carbaldehyde ,  1-(Phenylthio)-2-propanone ,  Trifluoromethanesulfonic acid

Reference (13)：

• 1) Padwa A., Gunn D. E., Jr., Osterhout M. H., Synthesis, 1997, 1353—1377 (1997).
• 2) Sano T., Trends Heterocycl. Chem., 7, 117—142 (2001).
• 3) Shinohara T., Toda J., Sano T., Chem. Pharm. Bull., 45, 813—819 (1997).
• 4) Shinohara T., Takeda A., Toda J., Terasawa N., Sano T., Heterocycles, 46, 555—565 (1997).
• 5) Shinohara T., Takeda A., Toda J., Ueda Y., Kohno M., Sano T., Chem. Pharm. Bull., 46, 918—927 (1998).

Terms in the title (6)： 超酸 ,  誘発 ,  環化反応 ,  キラル ,  ジメチル ,  テトラヒドロイソキノリン類