A facile two-step preparation of 4-alkoxy(or aryloxy)-3-arylisoquinolin-1(2H)-ones from 2-alkoxy(or aryloxy)methylbenzonitriles has been achieved. The benzylic carbanions, generated by deprotonation of the starting nitriles with lithium diisopropylamide (LDA) in diglyme at -78 °C, react with ethyl benzoates to give 2-alkoxy(or aryloxy)(aroyl)methylbenzonitriles. These aroylated benzonitriles can be converted into the corresponding desired isoquinolinones by hydrolysis under alkaline conditions followed by acidification of the resulting benzamide intermediates at room temperature.
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Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan;
