Synthesis, characterization and electrochemical study on new derivatives of 1,4-dihydroxyanthraquinone

Abstract

Electroorganic synthesis is recognized as an environmentally friendly methodology for the oxidation and the reduction of organic compounds, since dangerous and toxic redox reagents are replaced by electric current, and the overall energy consumption is reduced.1 In addition, it provides a means whereby unstable or hazardous reagents can be produced in situ and allows reactions to be carried out under mild conditions.2 Therefore, organic electrochemistry often provides interesting and useful alternatives to conventional synthetic methods and constitutes a useful tool for the organic chemist. Organic electrosynthesis can be regarded as a very versatile and mature field of organic synthesis. Hydroxyl derivative of anthraquinones is an important organic compound that is widely used in many fields such as antioxidant, dye, photography and pharmaceutical antitumor drugs such as doxorubicin3. With attention to these findings, we thought that presence of 1,4-dihydroxyanthraquinone and dimedone in one framework would be useful from the point of view of pharmaceutical properties and it is expected that these two moieties on one framework enhance the biological activity. The reaction of electrochemically generated anthradiquinone as a Michael acceptor with dimedone, as nucleophiles in ethanol/water mixtures has been studied by means of cyclic voltammetry and the desire product synthesis throuth electrolysis (Scheme 1). The electrosynthesis has been successfully performed in good yield and purity.