In this work, the new benzoxazinones and benzoxathiinones were synthesized from reaction of alkyl X-phenylpropiolates and aminophenol (or 2-mercaptophenol) in the presence of triphenylphosphine. Their antibacterial activities were studied against Gram-positive bacteria and Gram-negative bacteria using the disc diffusion method. The obtained results showed that these compounds are more effective against Gram-positive bacteria than against Gram-negative bacteria. Also, evaluation of antioxidant activity of the obtained products showed that they have high to excellent antioxidant activity (79.2–93.6%).