Studies on Tertiary Amine Oxides. LXXXI. Formation of 1-lsoquinoliniomethylides by the reaction of Isoquinoline 2-Oxide with Cyanoacetic Acid and Benzoylacetonitrile in the Presence of Acetic Anhydride

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概要

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• Isoquinoline 2-oxide (1) reacts with cyanoacetic acid in the presence of Ac_2O to afford various types of 1-substituted isoquinolines (2,4,6,and 7) and N-ylides (3 and 5a) depending upon the reaction conditions and processing procedures (Table I). The reaction in Ac_2O gives initially α-acetoxycarbonyl-1-isoquinolineacetonitrile (2) and 2-isoquinolinio-acetoxycarbonylcyanomethylide (3), and that in Ac_2O-dimethylformamide yields only 3. Products 2 and 3 are readily convertible into α-acetyl-1-isoquinolineacetonitrile (4) and 2-isoquinolinio-acetylcyanomethylide (5a), respectively, by processing involving heating. The reaction in ethanol gives ethyl α-cyano-1-isoquinolineacetate (6) and di (1-isoquinolyl) acetonitrile (7). The reaction of 1 with benzoylacetonitrile affords both the corresponding 1-substituted isoquinoline (10) and N-ylide (11). Reactions with ethyl benzoylacetate and, methyl and ethyl acetoacetates produce 1-substituted isoquinolines (12 and 14a, b) and 4-acetoxyisoquinoline (13), no ylide being formed.

• 公益社団法人日本薬学会の論文
• 1984-12-25

著者

• 舟越 和久

  Faculty of Pharmaceutical Sciences, Kyushu University

• 舟越 和久

  Faculty Of Pharmaceutical Sciences Kyushu University

• 浜名 政和

  Faculty of Pharmaceutical Sciences, Kyushu University

• 浜名 政和

  Faculty Of Pharmaceutical Sciences Kyushu University

• 稲田 治明

  Faculty of Pharmacutical Sciences, Kyushu University

• 稲田 治明

  Faculty Of Pharmacutical Sciences Kyushu University

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