Synthesis, characterization, and antimicrobial evaluation of novel 5-benzoyl- N -substituted amino- and 5-benzoyl- N -sulfonylamino-4-alkylsulfanyl-2-pyridones.

The present research describes the synthesis of novel 5-benzoyl- N -substituted-amino- and 5-benzoyl- N -sulfonylamino-4-alkylsulfanyl-2-pyridones 5a - c and 6a - c via the reaction of 2-benzoyl-3,3-bis(alkylthio)acrylonitriles 2a - c with N -cyanoacetohydrazide 3 and cyanoaceto- N -phenylsulfonylhydrazide 4 , respectively. Also, the reactivity of the compounds 5a - c toward hydrazine hydrate to give product 1 H -pyrazolo[4,3- c ]pyridine derivative 7 was studied. In addition, the reactivity of the 2a - c toward 1-cyanoacetyl-4 arylidenesemicarbazides 8a - c afforded 3,5-dihydro[1,2,4]triazolo[1,5- a ]pyridine-6-carbonitrile derivatives ( 12 - 14 ) a - c , which reacted with hydrazine hydrate to give 3 H -pyrazolo[4,3- c ][1,2,4]triazolo[1,5- a ]pyridine-6-carbonitrile derivatives 15a - c . The structures of the new products were characterized based on 1 H nuclear magnetic resonance, 13 C nuclear magnetic resonance, infrared, mass-spectroscopy, and elemental analyses. The products were screened in vitro for their antibacterial and antifungal activity properties.