Abstract
Direct amination of the anthraquinone nucleus was studied as a substitute for the Ullmann amination to synthesize aminoanthraquinone derivatives. In the presence of copper chlorides, 2-butylamination of 1,4-dihydroxyanthraquinone (DHAQ) proceeded quantitatively at ambient temperature. The effects of temperature, atmosphere, mole ratio of copper ions and the kinds of amines on the 2-amination of DHAQ were studied. The mechanism was proposed as follows: 2-amination of DHAQ was initiated by the formation of a copper complex between a DHAQ dianion and copper ions, which was disproportionated to give quinizarinquinone (QZQ) and metal copper by a redox system. The final Michael type addition of amine to QZQ gave a 2-aminated product. Both quantitative 2-amination of QZQ and reduction of copper ion to metal copper supported the mechanism.
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