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Short Paper | Regular issue | Vol 83, No. 11, 2011, pp.2635-2642
Published online, 6th October, 2011
DOI: 10.3987/COM-11-12348
A Convenient Synthesis of 4-Alkoxy(or Aryloxy)-3-arylisoquinolin-1(2H)-ones from 2-[Alkoxy(or Aryloxy)metnyl]benzonitriles

Kazuhiro Kobayashi,* Kota Matsumoto, Akihiro Kobayashi, and Miyuki Tanmatsu

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A facile two-step preparation of 4-alkoxy(or aryloxy)-3-arylisoquinolin-1(2H)-ones from 2-[alkoxy(or aryloxy)methyl]benzonitriles has been achieved. The benzylic carbanions, generated by deprotonation of the starting nitriles with lithium diisopropylamide (LDA) in diglyme at –78 ˚C, reacts with ethyl benzoates to give 2-[alkoxy(or aryloxy)(aroyl)methyl]benzonitriles. 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.