A new synthesis of 1-amino-4-butylaminoanthraquinone from 1-aminoanthraquinone promoted by metal ions.
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概要
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In the presence of some metal ions and atmospheric oxygen, 1-aminoanthraquinone(<B>1</B>) reacts readily with butylamine to give 1-amino-4-butylaminoanthraquinone(<B>2a</B>), along with a small amount of 1,4-diaminoanthraquinone, which is produced by the dealkylation of <B>2a</B>. The activity of the metal ions decreased in the following order: Co(II)>>Ni(II)>Cu(II)>Al(III). The reaction is remarkably affected by the substitution of an alkyl group into the amino group of <B>1</B>, the addition of a chelating agent, the counter anion of metal ions, and the reaction temperature. By the use of cobalt(II) chloride, the reaction proceeds most smoothly at about 30 °C. Both anthraquinone and 2-aminoanthraquinone show no sign of the reaction under the same conditions. A possible mechanism involving the formation of a metal complex, followed by the nucleophilic attack of amine at the 4-position and the oxidative abstraction of the hydride anion by atmospheric oxygen is proposed.
- 公益社団法人 日本化学会の論文
著者
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Yoshida Katsuhira
Department Of Chemistry Faculty Of Science Kochi University
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Matsuoka Masaru
Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture
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Yamashita Yoshio
Department of Chemistry, Faculty of Science, Kochi University
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Kitao Teijiro
Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture
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