02608nas a2200157 4500008004100000245008700041210006900128260000800197300001400205490000700219520209600226100001702322700002202339700002502361856006402386 2024 eng d00aSynthesis of pyrazole and 1,3,4-oxadiazole derivatives of pharmaceutical potential0 aSynthesis of pyrazole and 134oxadiazole derivatives of pharmaceu cAug a127–1350 v223 a

Heterocyclic compounds are important molecules that serve as scaffolds or linkers for the core structure of numerous drug substances. In particular, pyrazole and 1,3,4-oxadiazole are compounds of great interest due to their comprehensive biological activities and interesting structural features. Here, we described an efficient and economical synthetic route leading to N-phenyl substituted pyrazole and 1,3,4-oxadiazole derivatives. Retrosynthetic disconnective analysis showed that the N-phenyl substituted pyrazole can be obtained from chalcone, accessible from the respective aldehyde, and acetophenone. The disubstituted 1,3,4-oxadiazole can be constructed from the respective aldehyde, which originates from pyrrole-containing compound, and formyl chloride. Based on our retrosynthetic analysis, N-phenyl substituted pyrazole was obtained by cyclization of the respective chalcone with phenylhydrazine to give pyrazoline which was in turn converted into pyrazole by oxidative aromatization. Potassium carbonate and a catalytic amount of molecular iodine were used to oxidatively cyclize semicarbazones into 1,3,4-oxadiazoles in a transition metal-free process. Novel pyrazole and 1,3,4-oxadiazoles with potential biological activity are investigated as antituberculosis, anticonvulsant, antidiabetic, anticancer, and tyrosinase inhibitory agents.

1 aKadam, Mayur1 aJadhao, Nitin, L.1 aGajbhiye, Jayant, M. uhttps://prospects.wum.edu.pl/index.php/pps/article/view/235