10H-phenothiazines are synthesized via Smiles rearrangement. These prepared phenothiazines act as a base to prepare ribofuranosides by treating them with b- D-ribofuranosyl-1-acetate-2,3,5-tribenzoate. 10H-phenothiazines on refluxing with hydrogen peroxide in glacial acetic acid gave 10H-phenothiazine-5,5-dioxides. The synthesized compounds were evaluated for their antioxidative properties through in vitro studies, and they are also screened for their antimicrobial activity. The structure of the synthesized compounds has been established by elemental analysis and spectroscopic data.