Facile Synthesis and Antimicrobial Activities of Novel 1,4-Bis(3,5-dialkyl-4 H-1,2,4-triazol-4-yl)benzene and 5-Aryltriaz-1-en-1-yl-1-phenyl-1 H-pyrazole-4-carbonitrile Derivatives

Abstract

A group of novel 1,4-bis(3,5-dialkyl-4H-1,2,4-triazol-4-yl)benzene and 5-aryltriaz-1-en-1-yl-1-phenyl-1H-pyrazole-4-carbonitrile derivatives have been successfully synthesized and characterized by spectroscopic analyses. The triazenes were obtained in moderate yield by a coupling reaction between 5-aminopyrazol-4-carbonitrile and aryl diazonium chlorides, and their structures were confirmed by detecting the CN functional group in both IR and 13C NMR spectra. Conversely, the novel 1,4-bis(3,5-dialkyl-4H-1,2,4-triazol-4-yl)benzene derivatives were obtained using a previously unreported and facile pathway starting with p-phenylenediamine with selected triethyl orthoalkylates and then hydrazine monohydrate, followed by refluxing in triethyl orthoalkylates. The structure of the methyl derivative was confirmed by X-ray analysis. The synthesized compounds were tested and evaluated as antimicrobial agents.