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Chemoselective synthesis of quinoline N-oxides from 3-(2-nitrophenyl)-3-hydroxypropanones

✍ Scribed by Kentaro Okuma; Jun-ichi Seto; Noriyoshi Nagahora; Kosei Shioji

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
163 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

The reaction of 3-(2-nitrophenyl)-3-hydroxypropanones with Zn/NH 4 Cl gave the corresponding quinoline N-oxides in 80-90% yields. The reaction initiated the reduction of nitro group to afford the corresponding hydroxylamine, which intramolecularly condensed and followed by dehydration to give quinoline N-oxide. Although treatment of 2-nitrochalcone with Zn/NH 4 Cl in EtOH/H 2 O resulted in the formation of quinoline N-oxide in low yield, the reaction of 2-nitrochalcone with Sn/NH 4 Cl in refluxing EtOH/H 2 O afforded quinoline N-oxide in 80% yield.

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