8-Chloro-1-substituted-[1,2,4]triazolo[4,3-a]quinox aline s 6 underwent facile condensation with various hydrocarbon derivatives in the presence of TEBAC in acetonitrile was refluxed and afforded corresponding 8-chloro-1,4-substituted-[1, 2,4]triazolo[4,3-a]quinoxaline derivatives 7a- j. Their chemical structures were characterized using IR, H 1 NMR and Mass spectral studies. All the above compounds were screened for anti-microbia l activity, anti-oxidant activity and their bioassay showed them to possess significant antimic robial activity and anti-oxidant activity.