Synthesis of 3‐cyano‐2‐pyridone derivative and its utility in the synthesis of some heterocyclic compounds with expecting antimicrobial activity

Abstract

AbstractNew 2‐pyridone derivatives bearing p‐methoxyphenyl and p‐bromophenyl substituents at C‐4 and C‐6 were prepared smoothly by the one‐pot reaction in high yield, and in a comparatively short time, it reacted with phosphorous oxychloride to produce the corresponding chloro compound. The latter was reacted with several nitrogen nucleophiles such as sodium azide, hydrazine, acetohydrazide, and benzohydrazide to give tetrazolo, hydrazino, and triazolo derivatives, respectively. The reaction of hydrazino derivative with cyclopentanone, furan‐2‐carbaldehyde afforded the corresponding hydrazone derivatives. Cyclocondensation of the latter compounds with thioglycolic acid afforded the nicotinamide derivatives. 2‐Pyridone reacted with ethyl chloroacetate to afford chloroacetate and ethyl acetate derivatives. Ethyl acetate‐derivative reacted with hydrazine hydrate and gave the acetohydrazide derivative, it was condensed with p‐anisaldehyde and gave the 4‐methoxybenzylidene acetohydrazide derivative. Also, 2‐pyridone reacted with chloroacetic acid and or benzoyl chloride, afforded the benzoate derivative and 2‐((6‐(4‐bromophenyl)‐3‐cyano‐4‐(4‐methoxyphenyl) pyridin‐2‐yl) oxy) acetic acid, respectively. Structures of the products were confirmed using spectroscopic data and elemental analyses. Antibacterial activity of the synthesized compounds was evaluated against Escherichia coli and Staphylococcus aureus.