Friday, 27 October 2006
OLCC-McClain (Oakley-Lindsay Center)
261

Effective synthesis of various quinoxalines promoted by lithium carbonate under ionic liquid

Jong Wook Baek, Myung Gun Son, and Jong Chan Lee. Chung-Ang University, Seoul, South Korea

In recent years, among the various classes of heterocyclic compounds, quinoxalins seemed as important component of pharmacologically active compounds. Quinoxalines moeity on being found in structures are various antibiotics such as Echinomycin, Levomycin and Actinoleutin that are known to inhibit growth of gram-positive bacteria and are active against various transplantable tumors. In addition quinoxaline derivatives are also associated with a wide spectrum of biological activities ranging from anthelmintic and anticancer to antimicrobial, antifungal, and antidepressant. Consequently we were interested in the synthesis of quinoxalines. Our study is based in the presence of ionic liquid, [bmim]BF4. Surprisingly, despite being an interesting class of compound, Its synthesis under ionic liquid has not yet been well established, though few report dealing with the synthesis of quinoxalines have been reported. However other methods were obtained predominantly as long reaction time and limited materials. Our new method involved oxidation of ketones with HTIB([hydroxy(tosyloxy)iodo]benzene), followed by treatment of 1,2-phenylenediamine and lithium carbonate to give quinoxalines in high yield and for short reaction time. It is simple and easy to handle, and environmentally benign synthetic method due to advantages of ionic liquid.


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