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Chemoselective synthesis of quinoline N ‐oxides from 3‐(2‐nitrophenyl)‐3‐hydroxypropanones
Author(s) -
Okuma Kentaro,
Seto Junichi,
Nagahora Noriyoshi,
Shioji Kosei
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.485
Subject(s) - quinoline , chemistry , hydroxylamine , yield (engineering) , medicinal chemistry , nitro , oxide , dehydration , organic chemistry , alkyl , materials science , metallurgy , biochemistry
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. J. Heterocyclic Chem., (2010).
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