合成路线1

This compound has been obtained by two different methods: The reduction of 1,4-diamino-5,8-dihydroxyanthraquinone (I) or 1,5-diamino-4,8-dihydroxyanthraquinone (II) with Na2S2O4 and NaOH in water gives the leuco derivative (III), which is condensed with N,N-dimethylethylene-1,2-diamine (IV) in refluxing ethanol and reoxidized by air to yield 1,4-bis[2-(dimethylamino)ethylamino]-5,8-dihydroxyanthraquinone (V). Finally, this compound is treated with MCPBA in dichloromethane to afford the target bis-N-oxide. Alternatively, the reduction of tetrachlorophthalic anhydride (VI) with Zn and NaOH in water at 50-60 C gives 3,4,6-trichlorophthalic anhydride (VII), which is further reduced with Zn and NaOH in refluxing water to yield 3,6-dichlorophthalic anhydride (VIII). The reaction of (VIII) with KF and NaF at 260-27 ?C affords 3,6-difluorophthalic anhydride (IX), which is cyclized with hydroquinone (X) by means of AlCl3 and NaCl at 200 +/- 5 C to provide 1,4-difluoro-5,8-dihydroxyanthraquinone (XI). Finally, this compound is condensed with N,N-dimethylethylene-1,2-diamine (IV) in pyridine to afford the already reported 1,4-bis[2-(dimethylamino)ethylamino]-5,8-dihydroxyanthraquinone (V), which is oxidized with MCPBA as before.