Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Tertiary Amine Oxides. XVI. Reactions of Quinoline 1-Oxides with Compounds Containing Reactive Hydrogens in the Presence of Acetic Anhydride.
浜名 政和山崎 企善
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ジャーナル フリー

1963 年 11 巻 4 号 p. 415-421

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Quinoline 1-oxides were found to react smoothly with compounds containing reactive hydrogens in the presence of acetic anhydride, producing the corresponding 2-substituted quinolines. The yields were generally good to excellent in the reactions of ethyl cyanoacetate, 1, 3-indandione, diethyl malonate, diethyl nitromalonate, ethyl nitroacetate (e. g. ethyl α-cyano-2-quinolineacetate in 88% yield), but acetone, acetophenone or phenylacetonitrile could not enter into the reaction. The reaction of quinoline 1-oxide using benzoyl chloride instead of acetic anhydride and those of pyridine 1-oxides in the presence of acetic anhydride proceeded similarly but in much lower yields.
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© The Pharmaceutical Society of Japan
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