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Short Paper | Regular issue | Vol 85, No. 10, 2012, pp.2523-2529
Published online, 3rd August, 2012
DOI: 10.3987/COM-12-12544
Synthesis of 3-Substituted 4-Alkoxyisoquinolin-1-amines by the Reaction of 2-[Alkoxy(lithio)methyl]benzonitriles with Nitriles

Kazuhiro Kobayashi,* Kota Matsumoto, and Kosuke Ezaki

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

Abstract

It has been found that the reaction of 2-[alkoxy(lithio)methyl]benzonitriles, generated in situ from 2-(alkoxymethyl)benzonitriles and two equivalents of lithium diisopropylamide in diglyme at –78 ˚C, with aliphatic and aromatic nitriles provides an efficient method for the one-pot preparation of 3-substituted 4-alkoxyisoquinolin-1-amines.