合成路线: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.
参考文献标题:Process for the preparation of 1,4-bis[[2-(dimethylamino)ethyl]amino]-5,8-dihydroxyanthracene-9,10-dione
文献作者:Denny,W.A.; Lee,H.H.(BTG International Ltd.)
参考来源:WO 0005194
合成路线: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.
参考文献标题:A large-scale synthesis of the bioreductive drug 1,4-bis[[2-(dimethylamino)ethyl]amino]-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)
文献作者:Denny,W.A.; Lee,H.H.
参考来源:J Chem Soc - Perkins Trans I 1999,(19),2755
合成路线: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.
参考文献标题:An improved practical synthesis of leuco-1,4,5,8-tetrahydroxyanthraquinone
文献作者:Chang,P.; Chang,C.C.
参考来源:Synth Commun 1995,25(3),1893
产品链接: CAS No. 136470-65-0››