Abstract

Although many compounds have been prepared which contain the heterocyclic nucleus known as the quinoxaline nucleus, very little fundamental experimentation has been reported by way of expanding the chemistry of quinoxaline beyond the basic condensation reaction and its valuable use as a means of characterization, for example, the reaction of vicinal diketones with o-phenylenediamine. Also, no know effort has been made to assemble the chemistry of the quinoxalines into one paper for ready reference. Additional interest is concerned with the chemotherapeutic value of basically substituted quinoxalines^1; however, this aspect of the problem will not be discussed. The chemistry of quinoxaline has been reviewed, and a long term research program with the quinoxalines has been started. The original problem was to prepare vinylquinoxalines and thereby open the way for numerous reactions of the 1, 4 addition type. No vinylquinoxalines were obtained, but in seeking routes to these compounds other interesting reactions have been investigated. An improved method for preparing isonitrosoacetone has been developed. Some work has been done in an attempt to improve the preparation of 2-methyl-, and 2,3-dimethylquinoxalines from the isonitroso compounds. Bromination has been accomplished with 2,3-dimethylquinoxaline using N-bromosuccinimide. And an anil addition using quinoxaline and phenyllithium has been achieved.

Degree

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

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