Biologically active compounds play a key role in the fight against diseases affecting both human and animal living organisms, as well as plants. Finding out about new molecules with a potential biological effect, not yet described in the literature, is one of the most important aspects in the development of medicine and agriculture. Compounds showing desirable biological activity include heterocyclic moieties such as 1,3,4-oxadiazoles. The oxadiazole molecule is composed of two nitrogen atoms and one oxygen atom, forming a five-membered heterocyclic ring. Structures of this type have been successfully used in the treatment of various diseases in humans and animals, and play an important role in modern agriculture. It has been proven that many oxadiazole derivatives exhibit antibacterial, antiviral, blood pressure lowering, antifungal, antineoplastic, anticancer, antioxidant, anti-inflammatory and analgesic properties. In addition, compounds based on 1,3,4-oxadiazole can act as plant protection agents due to their herbicidal, insecticidal and fungicidal activity. Due to the constantly growing interest in heterocyclic systems of this nature, new methods of obtaining complex structures containing oxadiazole rings are sought. This article discusses various methods of synthesis of 1,3,4-oxadiazole derivatives exhibiting biological activity. Based on these techniques, these compounds could be used in the future in medicine and agriculture.

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by ¹H-NMR, ¹³C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.

A series of new symmetrical 2,5-dialkyl-1,3,4-oxadiazoles containing substituted alkyl groups at the terminal positions with substituents, such as bromine, isopropyloxycarbonylmethylamino, and carboxymethylamino, were successfully synthesized. The developed multistep method employed commercially available acid chlorides differing in alkyl chain length and terminal substituent, hydrazine hydrate, and phosphorus oxychloride. The intermediate bromine-containing 2,5-dialkyl-1,3,4-oxadiazoles were easily substituted with diisopropyl iminodiacetate, followed by hydrolysis in aqueous methanol solution giving the corresponding 1,3,4-oxadiazoles bearing carboxymethylamino substituents. The structure of all products was confirmed by conventional spectroscopic methods including ¹H NMR, ¹³C NMR, and HRMS.

New derivatives of 5-phenyl-1,3,4-oxadiazole substituted at position 2 with (bromomethyl)phenyl or bromoalkyl groups were obtained via microwave-assisted cyclodehydration of unsymmetrical N,N′-diacylhydrazines. Then, bromine-containing oxadiazoles were substituted with diisopropyl iminodiacetate, yielding the corresponding ester derivatives, which were subsequently hydrolyzed in an aqueous methanol solution. The cleavage of the ester group resulted in the formation of the appropriate 5-phenyl-1,3,4-oxadiazoles bearing bis(carboxymethyl)amino groups in satisfactory yields. The structures of all products were confirmed by typical spectroscopic methods including 1H and 13C NMR, and HRMS.