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

Abstract

New 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.

Efficient synthesis and biological evaluation of some new series of pyridine derivatives: Promising and potent new class of anticancer agents

“…Also, its 1 H NMR spectra showed disappearance of characteristic signals for NH 2 and revealed a singlet signal at δ 10.92 ppm for NH proton and showed the increase number of aromatic protons as illustrated in the experimental section also 13 C NMR displayed signals at δ 164.5, 166.2 ppm corresponding to C=O groups as well as all other signals appeared at their expected position as illustrated in the experimental part and the mass spectrum gave a molecular ion peak at m/z 502 (M + ; 6%). Schiff base 19 was obtained via the condensation of acetohydrazide derivative 12a with 4‐methoxybenzaldehyde [ 48 ] in ethanol under reflux; (Scheme 6).…”

Contemporary progress in the green synthesis of spiro-thiazolidines and their medicinal significance: a review

“…S. S. Shaban and co-researchers 86 synthesized spiro derivatives and some of them were checked against Gram-negative bacteria ( Escherichia Coli ) and Gram-positive bacteria ( Staphylococcus aureus ) via the disc diffusion method at 1 mg mL −1 disc concentration. Altogether, these derivatives displayed moderate to good antibacterial activity.…”

Bioactive 2-pyridone-containing heterocycle syntheses using multicomponent reactions

“…Recently, El-Hashasha and co-workers described the timeefficient synthesis of 4,6-diaryl-3-cyano-2(1H)-pyridone 48 by a four-component reaction of 4-methoxybenzaldehyde 1, 4bromoacetophenone 7, ethyl cyanoacetate 8, and an excess of ammonium acetate in reuxing ethanol for 20 min (Scheme 13A). 64 The precipitate was ltered, dried, and recrystallized from methanol to afford product 48 in 89% yield. The plausible mechanism reaction proceeds via a Knoevenagel condensation The condensation reaction of 1,5-dicarbonyl compound XI with ammonia gives enamine intermediate XII, which undergoes an intramolecular cyclization/dehydrogenation sequence to deliver the desired product 48.…”