In this study, a series of highly diversified novel functionalized spirooxindolopyrrolidine and spirooxindolopyrrolizidine-linked 1,2,3-triazole conjugates have been synthesized by a one-pot, four-component condensation of (E)-2-(1-propargyl-2-oxoindoline-3-ylidene)acetophenones as bifunctional dipolarophiles, acenaphthenequinone, α-amino acids with substituted aryl azides using coinage metal catalysts. It was found that CuSO₄/Na ascorbate as a catalyst was more performant than Ag₂CO₃ or CuI. The single-crystal X-ray analysis of one of the cycloadducts proves the structure and the regiochemistry of this reaction. The compounds have been screened for their in vitro antibacterial and antifungal activities using the agar dilution method and display good activities.