ABSTRACT

Synthesis and Antibacterial Activity of 1, 5-disubstituted tetrazoles (1-(2-Fluorphenyl)-5-phenyl- 1H-tetrazole, 1-(2-chlorophenyl)-5-phenyl-1H-tetrazole) in 87-88% yields using Zirconium Oxychloride in the presence of sodium azide and acetonitrile as solvent. With Zirconium Oxychloride and Sodium Azide was used as azide transfer reagent as it transformed the amide to imidoylazide intermediate and, then, by ring closing to tetrazole. The formation of hindered 1, 5- disubstituted tetrazoles was confirmed by1H-, 13C- and 19F-NMR, HRMS and FT-IR. A possible mechanism is described to clarify the effect of electron-withdrawing groups on anilines ring in the conversion to tetrazoles. In fact, substituent effect on nitrogen of amide group has key role in ring closing imidoylazide intermediate to tetrazoles. Keywords: 1, 5-Disubstituted tetrazoles, Zirconium Oxychloride and Sodium Azide, Acetonitrile, N-benzoyl amide
Publication date: 01/01/2024

https://ijbpas.com/pdf/2024/January/MS_IJBPAS_2024_7699.pdf

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https://doi.org/10.31032/IJBPAS/2024/13.1.7699