This article represents the development of a novel synthetic route towards the synthesis of s-triazine derivatives bearing benzimidazole and 1,2,4-oxadiazole cores (compounds 2-8a, b), which are interconnected through N- and O-spacers, via a nucleophilic substitution approach facilitated by C-N bond activation, using Pd(II) acetate as a catalyst. This methodology involves use of synthons such as imidate ester and oxime, towards synthesizing s-triazine derivatives. All synthesized compounds were characterized using 1H NMR, 13C NMR, and IR spectroscopy and validated through in-silico studies concerning cervical cancer. Density Functional Theory (DFT) study results showed that several factors should be considered when evaluating the suitability of the compounds studied as candidates for strong binding with proteins. For compounds 6b, 6d, and 8a the DFT results provided pronounced support for the in-silico and molecular docking studies. The Pd(II)-acetate-catalysed approach highlights the strategic utility of transition metal catalysis in constructing complex multi-heterocyclic framework that combine three biologically relevant pharmacophores within a single molecule, providing efficient access to diverse compounds with potential therapeutic applications in medicinal chemistry.