Nitrogen-containing heterocycles are central scaffolds in medicinal chemistry and are incorporated in most small-molecule drugs. We were interested in feasible strategies to synthesize nitrogen-rich heterocyclic scaffolds that can extend the currently available libraries with new drug-like molecules. Our past work on pyrazoles and triazoles motivated us to search for suitable and versatile strategies to explore access to triazole-pyrazole hybrids. Triazole-pyrazole hybrids, particularly non-fused heterocycles of this class, have not been investigated systematically.