N-Tosylhydrazones have been widely used as precursors of diazo compounds. A number of transition-metal-catalyzed and transition-metal-free transformations of N-tosylhydrazones via cyclopropanation, C–H insertion, ring expansion, coupling reactions, and construction of heterocycles have been demonstrated. Despite remarkable and excellent developments of novel protocols using N-tosylhydrazones in organic synthesis, there are no reports on the reactions of N-tosylhydrazones with 3-formylchromones for diverse and functionalized xanthones so far. Xanthones are important oxygenated heterocyles found in many natural products exhibiting prominent biological and pharmacological activities. Molecules bearing a xanthone moiety exhibit potent anticancer, antimicrobial, antimalarial, anti-HIV, antioxidant, anti-angiogenesis, antialzheimer, protein kinase C, α-glucosidase, and cholesterol acyltransferase inhibitory activities. In addition, some of these compounds are evaluated and utilized as major drug candidates. Although several approaches for the synthesis of xanthones have been well described, more facile and efficient protocols for diverse and functionalized xanthones are still highly desirable. Herein, we present simple and efficient base-promoted denitrogenative /deoxygenative/deformylative condensation for the regiospecific construction of biologically interesting polyfunctionalized xanthones starting from N-tosylhydrazones and two molecules of 3-formylchromones (Scheme 1) This protocol proceeds via cascade diazo formation/Michael addition/ring cleavage/Michael addition/intramolecular aldol condensation/aromatization. The synthesized xanthones were also screened for potent UV-filters, fluorescent sensors, and antioxidant properties.