Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Ring Contraction of 3-Hydroxyquinolines to Oxindoles with Hydrogen Peroxide in Acetic Acid
TOSHIAKI NAKASHIMAIKUO SUZUKI
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1969 Volume 17 Issue 11 Pages 2293-2298

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Abstract
8-Nitroquinoline (I) was contracted to 7-nitrooxindole (III) via 3-hydroxy-8-nitroquinoline (II) with hydrogen peroxide in acetic acid. 3-Hydroxyquinoline-8-carboxylic acid (XIV) and its ethyl ester (XV) were also contracted to oxindole-7-carboxylic acid (XVI) and its ethyl ester (XVII), respectively, in the same conditions. On the other hand, 3-hydroxyquinoline and 3-hydroxy-8-methylquinoline (XX) did not undergo contraction in the above conditions.
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© The Pharmaceutical Society of Japan
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