Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabutylammonium bromide, which plays the role of a phase-transfer catalyst. The luminescence properties of the obtained compounds are discussed in the context of applying these compounds in optoelectronics. Specifically, two highly-conjugated final products: N,N-dimethyl-2-phenyl-6-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)quinazolin-4-amine (8f) and 6,6′-(4,4′-(1,3,4-oxadiazole-2,5-diyl)bis(4,1-phenylene))bis(N,N-dimethylquinazolin-4-amine (9f), which contain a 1,3,4-oxadiazole moiety connected to a quinazoline ring by a 1,4-phenylene linker at the 6 position, exhibit strong fluorescence emission and high quantum yields.

Two novel series of symmetrical and unsymmetrical conjugates, in which 1,3,4-thiadiazole and 4-N,N-dimethylaminoquinazoline scaffolds were connected via 1,4-phenylene linker, were synthetized in high yields by Suzuki cross-coupling reactions. The elaborated protocol makes use of bromo-substituted quinazolines, boronic acid pinacol ester or diboronic acid bis(pinacol)ester of 2,5-diphenyl-1,3,4-thiadiazole, catalytic amounts of [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) Pd(dppf)Cl₂, sodium carbonate, and tetrabutylammonium bromide, which plays the role of a phase-transfer catalyst. The structures of prepared compounds were confirmed by ¹H NMR, ¹³C NMR, UV-VIS, IR and HRMS. For the target compounds, the fluorescence spectra were measured to determine their quantum yields and Stokes shifts. The study revealed that among the tested compounds, two highly-conjugated derivatives (8a, 9a), in which 1,3,4-thiadiazole core is connected to 4-(N,N-dimethylamino)quinazoline via a double 1,4-phenylene linker, exhibit high quantum yields of fluorescence and strong fluorescence emission.

1,3,4-Oxadiazoles containing boronic acid moieties are promising as a highly versatile class of compounds with significant utility across various scientific domains. The diverse synthetic methodologies for their preparation make these compounds valuable precursors for developing novel entities with tailored properties in medicinal chemistry, agrochemistry, and materials science. This review systematically compiles and discusses synthetic methods for the direct and indirect incorporation of boronic acid derivatives into 1,3,4-oxadiazole scaffolds. Understanding these strategies is particularly important because of their key role in modern synthetic transformations, especially Suzuki–Miyaura cross-coupling reactions, which enable easy access to a new generation of structurally diverse 1,3,4-oxadiazole-based compounds. The synthetic procedures and reactions discussed are based on the currently available literature, offering a comprehensive overview of this rapidly evolving field.