Chemoselective Synthesis of Quinoline N-Oxides from 3-(2-Nitrophenyl)-3-hydroxypropanones

[摘要]：The reaction of 3-(2-nitrophenyl)-3-hydroxypropanones with Zn/NH4Cl 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/NH4Cl in EtOH/H2O resulted in the formation of quinoline N-oxide in low yield, the reaction of 2-nitrochalcone with Sn/NH4Cl in refluxing EtOH/H2O afforded quinoline N-oxide in 80% yield.

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