Abstract
The reaction of 1,4-Dihydroxyanthraquinone with diamines was carried out in the presence of CuCl(2), CuCl in the ionic liquid [Bmim]PF(6), [Bmim]BF(4) or [Bmim]Cl x CuCl.
Highlights
There is currently renewed interest in aminoanthraquinones
As part of a program to investigate the range of organic reactions possible in ionic liquids, we examined the reactions of 1,4-dihydroxyanthraquinone and diamines NH2RNH2 in ionic liquids (Scheme 1)
We found that in the presence of 20 mol % CuCl2, the reaction of 1,4-dihydroxyanthraquinone and ethylenediamine in the ionic liquid [Bmim]PF6 resulted in the formation of 6-hydroxy-1,2,3,4-tetrahyronaphtho[2,3-f]-quinoxaline-7,12-dione in 99% yield, and that the reaction proceeded smoothly at room temperature and was complete within 2 hours
Summary
There is currently renewed interest in aminoanthraquinones. The use of mono- and diaminothraquinones in the dyestuffs industry has been well established for many years, but recently a number of other features of aminoanthraquinone chemistry have attracted intense interest. Abstract: The reaction of 1,4-Dihydroxyanthraquinone with diamines was carried out in the presence of CuCl2, CuCl in the ionic liquid [Bmim]PF6, [Bmim]BF4 or [Bmim]Cl·CuCl. There is currently renewed interest in aminoanthraquinones. Our recent research interests have been in the development of new synthetic method using ionic liquids as reaction media and promoters [7].
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