Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Deoxygenation of Heterocyclic N-Oxides by Chromium (II) Chloride
秋田 安男三須 恵子渡辺 徳弘太田 明広
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1976 年 24 巻 8 号 p. 1839-1841

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N-Oxides of pyridine, quinoline, and pyrazine derivatives were reduced with chromium (II) chloride in acetone, methanol, or chloroform at room temperature to give the deoxygenation products in excellent yields. Quinaldine and 2-ethoxyquinoline 1-oxides, possessing an electron donating group at 2-position of the quinoline ring, were not reduced at room temperature, but, under reflux, the reaction gave the deoxygenation products in good yields. In the case of the reaction of 4-chloroquinoline 1-oxide with chromium (II) chloride for 20 min occured dechlorination and deoxygenation, but for 1 min only deoxygenation. The reaction of 4-nitropyridine 1-oxide and 3-, 4-, and 5-nitroquinoline 1-oxides was not successful.
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© The Pharmaceutical Society of Japan
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