This work summarizes one-pot synthetic approaches to spiro-fused (di)azoles, which are promising in terms of studying biological activity. Proposed approaches involve condensation reactions of (hetero)cyclic ketones, methylene active moieties, and N-nucleophiles, occurring under mild conditions by both stepwise and concerted mechanisms. The antimicrobial activity of signals from the proposed approaches of cyanosubstituted spiro-membered pyrazolines and pyrrolidines against gram-negative (P. aeruginosa, E. coli) and gram-positive (S.