E. Darwish, Khalid A. Atia, A. Farag
Jun 1, 2014
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Influential Citations
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Journal
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry
Abstract
The versatile hitherto unreported 2-cyano-N-(4-{[(5-methylisoxazol3-yl)amino]sulfonyl}phenyl)acetamide (3) was utilized for the synthesis of a variety of heterocycles incorporating sulfamoyl moiety. The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with pentane-2,4-dione, arylidenes malononitrile, or terephthalaldehyde and malononitrile upon heating under reflux in the presence of a catalyst. Condensation of the cyanoacetamide 3 with salicylaldehyde furnished the corresponding chromene derivatives. Coupling of 3 with arene diazonium chlorides gave the hydrazone derivatives 13a-c, which upon treatment with hydrazine hydrate and ethyl chloroformate furnished the corresponding pyrazole and triazine derivatives, respectively. Reaction of 3 with carbon disulfide and 1,2-dibromoethane, 1,3-dibromopropane or dimethyl sulfate afforded 2-cyano-2-(1,3-dithiolan-2-ylidene)-N-(4-{[(5-methylisoxazol-3yl)amino]sulfonyl}phenyl)acetamide (18), 2-cyano-2-(1,3-dithian-2-ylidene)-N4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide (19), and 2-cyanoN-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)-3,3-bis(methylthio)acrylamide (20). The newly synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities, and showed promising results. INTRODUCTION Cyanoacetamides are highly reactive bifunctional compounds. The carbonyl and the cyano functions of these compounds are suitably situated to enable reactions with common reagents to form a variety of heterocycles. Also, the active methylene of cyanoacetamide can take part in a variety of condensation and substitution reactions. Moreover, cyanoacetamides and their related heterocyclic derivatives have attracted great attention due to their interesting biological, therapeutic value and pharmaceutical activities HETEROCYCLES, Vol. 89, No. 6, 2014 1393