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

被引:13
作者
EL-Hashash, Maher A. [1 ]
Shaban, Safaa S. [1 ]
Ali, Rania S. [2 ]
机构
[1] Ain Shams Univ, Sci Fac, Chem Dept, Heterocycl Synthet Lab, Cairo 11566, Egypt
[2] Helwan Univ, Fac Technol & Educ, Dept Basic Sci, Cairo, Egypt
关键词
BIOLOGICAL EVALUATION; ANTICANCER; DESIGN; SERIES;
D O I
10.1002/jhet.4175
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:329 / 339
页数:11
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