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Note | Regular issue | Vol 63, No. 12, 2004, pp.2859-2862
Published online, 29th October, 2004
DOI: 10.3987/COM-04-10228
Palladium(II)-mediated Nucleophilic Cyanation of 4-Substituted Quinoline 1-Oxide in the Presence of Trimethylsilyl Cyanide and an Oxidant

Yoshinobu Tagawa,* Yoshitaka Higuchi, Kenji Yamagata, Kazuhiko Shibata, and Daisuke Teshima

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan

Abstract

Reaction of 4-substituted (electron-releasing group) quinoline 1-oxides (1) with trimethylsilyl cyanide in the presence of palladium(II) acetate and DDQ gave 2-cyano-4-substituted quinoline 1-oxides (2) in THF in moderate yields. It was reasoned that this reaction proceeds through palladium-catalyzed dehydrosilylation.