A library of 12 members of 3,4-dihydro-2H-benzo[b][1,4]oxazines has been synthesized from substituted 2-aminophenols, benzaldehydes and phenacyl bromides via one-pot multicomponent reactions using Cs2CO3 as a base catalyst, by both conventional and microwave-assisted heating. Microwave assistance reduced the reaction time and solvent, improved the yield, purity, and made the work-up easier. The results suggested that the products possess moderate to good antibacterial activity. These findings imply that the synthesized compounds may make excellent candidates for further studies aimed at discovering novel antibacterial agents. In vitro antioxidant qualities of the synthesized oxazines are evaluated. In the tests for reducing power and radical scavenging, all the compounds demonstrated strong antioxidant activity--even surpassing that of the positive control, Trolox.