| Since anthracycline compounds and derivatives in the clinical application and its unique chemical structure making it the best interest of this chemical synthesis fields. Anthracene derivatives have anti-tumor, anti-bacterial and anti-inflammatory, anti-virus and other pharmacological effects, used in the treatment of acute leukemia, breast cancer, lung cancer, bladder cancer and other cancers. In the application of the organic field-effect transistor, anthracene derivative is also an important semiconductor material and call luminescent material. Some data indicates that, hydroxy-substituted anthracene-based compounds are important intermediates for these drugs are converted in vivo and anthraquinone derivatives of the plant generation. Therefore hydroxy substituted anthracene-based compound has an important meaning for the chemical synthesis of these drugs and toxicity studies, at the same time can also be used to improve the performance of ion channels and a liquid crystal material.The experiments on the basis of previous studies, synthesized several hydroxy anthracene compounds. In this experiment, the anthraquinone, phthalic anhydride, phenol, etc. as a starting material, synthesized a series of compounds of the the hydroxy anthraquinone or aminoanthraquinone and derivatives by acylation, nitration, Friedel-Crafts alkylation reaction.Hydroxyanthracene compound thus obtained is purified and then in a reducing agent under the action of the sulfite, sodium borohydride, zinc and others. Finally, the target compounds were characterized. As the individual compounds structurally and chemically different, so using a different route of synthesis and purification methods.1) Anthraquinone as raw material, obtained1-nitroanthraquinone by nitration of the mixed acid, recrystallized to obtain a high-purity1-nitroanthraquinone. In this raw material, through reduction in the system of THF to give I-aminoanthraquinone, under basic conditions, with zinc dust to give1-aminoanthracene decarbonylation. Finally, through the reduction of sodium bisulfite to give1-aminoanthracene. This experiment on the basis of previous studies, the intermediate product was purified. Explore the recrystallization conditions for each of the intermediate product, the final target product was obtained. Structure confirmed by means of IR,1H-NMR.2) Phthalic anhydride and hydroquinone as raw materials, got through the Friedel-Crafts acylation reaction cyclization under the action of a strong acid to give1,4-dihydroxyanthraquinone. Prepared under the sodium borohydride reduction of1,4-dioneanthracene. After recrystallization,further reduction by hydrosulfite the prepared target product1,4-dihydroxyanthracene. This method overcomed the problem of1,4-dihydroxyanthraquinone process for preparing concentrated sulfuric acid was easy oxidation of hydroquinone, and the reaction intermediates and the final product was easily oxidized.Finally obtained1,4-dihydroxyanthraquinone, structure confirmed by means of IR,1H-NMR.3) Anthraquinone as raw material, obtained1,5-dinitroanthraquinone and1,8-dinitroanthraquinone by nitration of the mixed acid. After initial impurity depending on both the solubility in high-boiling organic solvent,1,5-dinitroanthraquinone and1,8-dinitroanthraquinone was separated.1,5-dimethoxyanthraquinone and1,8-dimethoxy--anthraquinone were prepared by the reduction of1,5-dinitroanthraquinone and1,8-dinitroanthraquinone by methanol and alkali.Under the reduction of sodium borohydride,1,5-dimethoxyanthraquinone was reduced to1,5-dimethoxyanthracene.1,8-dimethoxyanthraquinone was reduced by zinc powder to give1,8-dimethoxyantho--xyanthracene. After hydrobromic deprotection to obtain the objective product1,8-dihydroxyanthracene. The final product was confirmed by means of such as IR,1H-NMR structural confirmation. |
