Abstract: Because the general small quinone molecules are fatsoluble compounds.They are insoluble in water and cannot be directly intravenous administration.Thus their clinical application is limited.To enhance the quinone molecular polarity and solubility,improving the biological structure of the mother,the quinones mother ring were tried to introduce hydrophilic glucose amino.The nucleophilic addition reaction of the aromatic ring with different structure types and the effect of glucosamine on the ortho and para quinones were investigated respectively.Tetrachloroquinone,2,3dichloro1,4naphthoquinone,1,4naphthoquinone,alizarin,alizarin red and glucosamine hydrochloride were used as a raw material,morphine and furfurylamine were used as auxiliary material.First,glucosamine was reacted with an equimolar amount of quinones to obtain monoglucosamino substituted trichlorobenzoquinone (b).Then (b) was reacted with an equimolar amount of furfuryl amine or morpholine to produce the glucosaminobenzoquinones (d) and (e) with a heterocyclic structure.The reaction between an equimolar amount of glucosamine and 2,3dichloro1,4 naphthoquinone can generate a single glucosaminosubstituted naphthoquinone (i).Compounds (h),(k),(m) and (n) can be produced by the additionoxidation method of reaction between an equimolar amount of glucosamine and 1,4naphthoquinone or alizarin or alizarin red.The yield of additionoxidation method is higher than that of haloquinone method,and the separation operation is relatively simple.All products were characterized by IR,UV,NMR and MS.

Key words: benzoquinone, naphthoquinone, anthraquinone, glucosamine, synthesis