Substitutions of Fluorine Atoms and Phenoxy Groups in the Synthesis of Quinoxaline 1,4-di-N-oxide Derivatives

The unexpected substitution of fluorine atoms and phenoxy groups attached toquinoxaline or benzofuroxan rings is described. The synthesis of 2-benzyl- and 2-phenoxy-3-methylquinoxaline 1,4-di-N-oxide derivatives was based on the classical Beirut reaction.The tendency of fluorine atoms linked to quinoxaline or benzofuroxan rings to be replacedby a methoxy group when dissolved in an ammonia saturated solution of methanol wasclearly demonstrated. In addition, 2-phenoxyquinoxaline 1,4-di-N-oxide derivativesbecame 2-aminoquinoxaline 1,4-di-N-oxide derivatives in the presence of gaseousammonia