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Short Paper | Regular issue | Vol 85, No. 4, 2012, pp.887-894
Published online, 22nd February, 2012
DOI: 10.3987/COM-12-12419
Synthesis of 3-Substituted 4-Sulfanyl-8-methoxyisoquinolin-1(2H)-ones by the Reaction of Ethyl 2-[Lithio(sulfanyl)methyl]-6-methoxybenzoates with Aliphatic and Aromatic Nitriles

Kazuhiro Kobayashi,* Hiroo Hashimoto, and Kazuhiro Nakagawa

*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 convenient method for the synthesis of 3-substituted 4-alkyl(or aryl)sulfanyl-8-methoxyisoquinolin-1(2H)-ones has been developed. Ethyl 2-(alkyl(or aryl)sulfanyl)methyl-6-methoxybenzoates, prepared by the reaction of readily available ethyl 2-halomethyl-6-methoxybenzoates with sodium thiolates, are deprotonated on treatment with lithium diisopropylamide (LDA) to generates the corresponding benzyl anions, which react cleanly with a variety of nitriles to provide generally good yields of the corresponding desired isoquinolin-1(2H)-ones.