“Quinoxaline and allied compounds”: Novel reactions and synthetic perspectives

ORGN 804

Ralph Nicholas Salvatore, ralph.salvatore@lehman.cuny.edu and Jason Hovland. Department of Chemistry, Lehman College-City University of New York, Davis 318, 250 Bedford Pk. Blvd. W, Bronx, NY 10468
Nitrogen-containing heterocyclic compounds are indispensable structural units in chemistry and biochemistry. Among the various classes of heterocyclic compounds, quinoxalines form an important component of pharmacologically active compounds. The quinoxaline ring is part of various antibiotics and is 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, antidepressant, antibacterial and anti-inflammatory activities, but also as herbicides, fungicides and insecticides. Recently, we reported an efficient, rapid, and facile reduction procedure of substituted quinoxalines via a one-pot process after the preparation of the quinoxaline via a “green chemistry” approach to afford tetrahydroquinoxaline derivatives. As an extension of our studies, biquinoxalines were synthesized and reduced respectively. Our reduction protocol employed MBH4,RX in anhydrous THF as the solvent of choice, generating, presumably, in-situ borane. Our method detracts from the traditional synthetic procedures and offers a "green" credential. Furthermore, this methodology demonstrates fast reaction times, high yields, and easy purification, if required. The synthesis and reduction of numerous structurally diverse quinoxalines and allied compounds will be discussed. Applications of quinoxalines in Coordination chemistry will also be presented.