A Pd-catalyzed one-pot cascade consisting of C-C/C-O/N-N bond formation to access clinically important fused 1,2,3-triazoles using N-aryl-α-(tosylhydrazone)acetamides with isocyanide has been developed. Besides, various substitutions on the N-aryl part of acetamides along with different isocyanides show good compatibility in this protocol. Next, two plausible mechanistic routes were proposed; however, one of the routes was more favourable which involved the formation of a benzoxazine ring first followed by the realization of a triazole ring. Additionally, the more favourable mechanistic route was investigated using DFT studies which suggests that the formations of a Pd(II)-isocyanide complex and α-diazoimino intermediates were key steps in the catalytic cycle.