Synthesis Of Fatty Amine Substituted Anthraquinones And Their Precursory Compounds

A series of fatty amine substituted anthraquinones and their precursory compounds was designed and synthesized on the basis of mechanism of bio-reductive antitumor drugs.N-alkylation and amination from the amino- and hydroxyl- anthraquinones as the starting materials reacting with epoxy compounds and primary fatty amines was investigated from the possible mechanism and a large extent of reaction conditions. 1-amino and 1, 4-diamino anthraquinones reacting with epichlorohydrin provided a series of (epoxypropylamino)anthraquinones. Prepared intermediate (3-chloro-2-hydroxylpropylamino)anthraquinone was proceeded with ring-closing reaction, hydrolysis reaction and amination reaction to give corresponding products. (Tosyloxy)anthraquinone analogues were synthesized from 1,4-di and 1,4,5,8-tetra hydroxyanthraquinone by condensation reaction with p-toluenesulsulfonyl chloride under base catalysts. The usage of these intermediates as precursors is an effective path for the synthesis of aminoanthraquinones which are unreadily available from hydroxyanthraquinones.For the further exploration to the useful intermediates of aminoanthraquinones, Selective protection of hydroxyanthraquinones and aminoanthraquinones, oxidation of hydroxyanthraquinones and iodination of anthraquinone were examined under some preliminary reaction factors.In addition, we have prepared the precursory compounds of bio-reductive antitumor reagent AQ4N and purify aromatic anhydride derivatives-pyromellitic dianhydride by using forming-complex.