New Synthetic Approaches to Substituted Pyridine-2-(1H)-ones Clubbed with Substituted Aryl Diazo Substituents

Abstract

6-Triazolylpyridone derivatives were synthesized by coupling 4-(4-methoxyphenyl)-6-(1H-1,2,4-triazol-1-yl)-1-(3-chlorophenyl)pyridin-2(1H)-one with substituted benzenediazonium chlorides in the form of two isomers, which were separated by column chromatography and characterized by ¹H and ¹³C NMR. Following the green approach, solvents were avoided as much as possible. The reaction monitoring was carried out by gas chromatography as well as thin-layer chromatography. The scope and limitation of the method are discussed. The structures of all the compounds have been assigned unambiguously on the basis of elemental analysis, infrared, and NMR spectral data and have been evaluated for antimicrobial and antitubercular activities.

GRAPHICAL ABSTRACT

Keywords:

• Aryldiazonium chlorides
• β-aryl glutaconic acid
• microbial activity
• 2-pyridones
• 1,2,4-triazole

ACKNOWLEDGMENTS

The authors thank the head, Department of Chemistry, for laboratory facilities. One of us (R. D. S.) is grateful to Veer Narmed South Gujarat University for financial support and for FTIR spectra. We also thank Rajani Microcare Laboratory, Surat, for antimicrobial and antitubercular activities, CDRI Lucknow for elemental analysis, and SAIF Chandigarh for ¹ H and ¹³ C NMR spectral analysis.

Notes

# Satisfactory C, N, and H analysis were obtained for all the compounds.