Methoxide Promoted Anionic Cyclization of 2-Alkynylbenzonitrile:A New Synthesis of 3-Substituted Isoqunolin-1-one |
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Authors: | Ming-Jung Wu Li-Juan Chang Chi-Fong Lin |
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Institution: | School of Chemistry, Kaohsiung Medical College, Kaohsiung, Taiwan |
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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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