Tetrahedron

A direct anionic cyclization of 2-alkynylbenzonitrile to 3-substituted-1 (2H)-isoquinolones and 3-benzylideneisoindol-2-ones initiated by methoxide addition

MJ Wu, LJ Chang, LM Wei, CF Lin

Index: Wu, Ming-Jung; Chang, Li-Juan; Wei, Li-Mei; Lin, Chi-Fong Tetrahedron, 1999 , vol. 55, # 46 p. 13193 - 13200

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Citation Number: 52

Abstract

Treatment of 2-(2-alkylethynyl) benzonitrile with sodium methoxide in refluxing methanol for 12 h gave 3-alkyl-1 (2H)-isoquinolone in modest yield. Under the same reaction conditions, methanolysis of 2-(2-arylethynyl) benzonitrile lead to the formation of 3-alkylidene isoindol-1- one. Partial hydrolysis of 2-(1-hexynyl) benzonitrile to the corresponding benzamide, followed by treatment of the benzamide with sodium methoxide in refluxing methanol gave ...

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