Bulletin of the Chemical Society of Japan p. 2735 - 2738 (1981)
Update date:2022-09-26
Topics:
Takei, Toshio
Matsuoka, Masaru
Kitao, Teijiro
The reaction of 1,4-dihydroxyanthraquinone (DHAQ,1) with various diamines were carried out in the presence of CuCl2.Primary 1,2-ethylenediamines or 1,2-cyclohexanediamine afforded the ring-closure products, 6-hydroxy-1,2,3,4-tetrahydronaphtho<2,3-f>quinoxaline-7,12-dione derivatives, in good yields of 70-98percent.On the other hand, in the cases of N-alkylethylenediamines or 2-(alkylamino)ethanols, the major products were the 2-aminated 1,4-dihydroxyanthraquinones.The direct 2-amination of 1 was greatly inhibited when an alkyl group was introduced to the amino group because of its steric requirement.The role of copper ions, the effect of a steric requirement of the N-alkyl substituent of amines, and the effect of the chain length of alkanediamines in the reaction of 1 with amines were studied.It was proposed that the reaction was initiated by the direct 2-amination of 1 via the copper complex, followed by the intramolecular nucleophilic substitution of the 2-amino group on the 2-alkylamino substituent to give the ring-closure product.
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