Synthesis of pyrazole and 1,3,4-oxadiazole derivatives of pharmaceutical potential

Mayur Kadam; Nitin L. Jadhao; Jayant M. Gajbhiye

doi:10.56782/pps.235

Published : 2024-08-21

Vol. 22 No. 3 (2024)

Synthesis of pyrazole and 1,3,4-oxadiazole derivatives of pharmaceutical potential

Mayur Kadam

Nitin L. Jadhao

Jayant M. Gajbhiye

DOI: https://doi.org/10.56782/pps.235

Abstract

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.

Keywords:

pyrazoline, pyrazole, oxidative aromatization, 1,3,4-oxadiazole, oxidative intramolecular cyclization

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Kadam, M., Jadhao, N. L., & Gajbhiye, J. M. (2024). Synthesis of pyrazole and 1,3,4-oxadiazole derivatives of pharmaceutical potential. Prospects in Pharmaceutical Sciences, 22(3), 127–135. https://doi.org/10.56782/pps.235

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Mayur Kadam

mayur.kadam9970@gmail.com

Affiliation:

a:1:{s:5:"en_US";s:7:"Student";} India

Nitin L. Jadhao

Affiliation:

CSIR-National Chemical Laboratory, Dr Homi Bhabha Rd, Ward No. 8, NCL Colony, Pashan, Pune, Maharashtra 411008, India India

Jayant M. Gajbhiye

Affiliation:

CSIR-National Chemical Laboratory, Dr Homi Bhabha Rd, Ward No. 8, NCL Colony, Pashan, Pune, Maharashtra 411008, India India