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

Abstract

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 1H-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 3H-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 1H nuclear magnetic resonance,13C nuclear magnetic resonance, infrared, mass-spectroscopy, and elemental analyses. The products were screened in vitro for their antibacterial and antifungal activity properties.