The present work aimed to study the potential of well-known synthetic strategies for the synthesis of imidazo[4,5-b]pyridine-derived (or 1-desazapurine-derived), purine-derived and benzimidazole-derived moieties and their modifications. This includes [3+3] cyclocondensations, inverse electron-demand Diels-Alder reaction, intramolecular palladium-catalyzed arylation. In addition, unprecedented method of synthesis of 4-trifluoromethylpyridines was developed, including scope limitation and theoretical mechanistic studies with DFT methods.