A series of 6-amino-substituted pyridine-2-(1H)-ones have been prepared by coupling of substituted 6-(pyrrolidin-1-yl)-2(1H)-pyridinones with aryl diazonium chlorides. The overall sequence provides a simple and efficient route to prepare 6-amino-substituted pyridine-2-(1H)-ones in the form of two isomers, which were separated using column chromatography. The structure of all the compounds has been assigned unambiguously on the basis of elemental analysis, IR and NMR spectral data and has been evaluated for antibacterial and antifungal activities. The active compounds were evaluated for antitubercular activity and compared with standard drug rifampicin.