Mech bis(bromomethyl)quinoxaline-1-N-oxide rxn amine via sub effect

Abstract

Rxn of bis(bromomethyl)quinoxaline N-oxides with amines is interesting from a rxn mechanism due to the reported biological activity of this class. The complex mechanism of this rxn (particularly in the case of primary amine) is complicated further when C6 or C7 sub mono-N-oxide are considered. The synth & subsequent characterization of a series of 2,3-bis(bromomethyl)quinoxaline-1-N-oxide is reported. Exptl and calcd evidence is used to show that the observed product ratios from the rxn with Et2NH reflect the influence of both the C6/C7 sub & the N-oxide group on the initial nucleophilic sub.