高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 35.

• Organic Synthesis Chemistry • 上一篇    下一篇

Methoxide Promoted Anionic Cyclization of 2-Alkynylbenzonitrile:A New Synthesis of 3-Substituted Isoqunolin-1-one

Ming-Jung Wu, Li-Juan Chang, Chi-Fong Lin   

  1. School of Chemistry, Kaohsiung Medical College, Kaohsiung, Taiwan
  • 出版日期:1998-12-31 发布日期:1998-12-31

Methoxide Promoted Anionic Cyclization of 2-Alkynylbenzonitrile:A New Synthesis of 3-Substituted Isoqunolin-1-one

Ming-Jung Wu, Li-Juan Chang, Chi-Fong Lin   

  1. School of Chemistry, Kaohsiung Medical College, Kaohsiung, Taiwan
  • Online:1998-12-31 Published:1998-12-31

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摘要： The treatment of 2-(2-alkylethynyl)benzonitrile with sodium methoxide in methanol gave 3-alkyl-l(2H)-isoquinolinone in modest yield. Under the same reaction conditions methanolysis of 2-(2-arylethynyl)benzonitrile lead to the formation of 3-alkylidene isoindol-1-one. Partially hydrolysis of 2-(l-hexynyl)benzonitrile to the corresponding benzamide,followed by the treatment of the benzamide with sodium methoxide gave 3-pentylidene isoindol-1-one in 11% yield. This result suggests that benzamide is not the intermediate of the formation of isoquinolinone. The more plausible mechanism of this methanolysis process is involving the iminium anion cycloaromatization to form 2-methoxyisoquinoline and subsequent hydrolyze to isoquinolinone. In one case,2-methoxyisoquinoline product was isolated.

Abstract: The treatment of 2-(2-alkylethynyl)benzonitrile with sodium methoxide in methanol gave 3-alkyl-l(2H)-isoquinolinone in modest yield. Under the same reaction conditions methanolysis of 2-(2-arylethynyl)benzonitrile lead to the formation of 3-alkylidene isoindol-1-one. Partially hydrolysis of 2-(l-hexynyl)benzonitrile to the corresponding benzamide,followed by the treatment of the benzamide with sodium methoxide gave 3-pentylidene isoindol-1-one in 11% yield. This result suggests that benzamide is not the intermediate of the formation of isoquinolinone. The more plausible mechanism of this methanolysis process is involving the iminium anion cycloaromatization to form 2-methoxyisoquinoline and subsequent hydrolyze to isoquinolinone. In one case,2-methoxyisoquinoline product was isolated.

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