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Paper | Regular issue | Vol 89, No. 6, 2014, pp.1393-1411
Published online, 16th April, 2014
DOI: 10.3987/COM-14-12954
Synthesis and Antimicrobial Evaluation of Some Isoxazole Based Heterocycles

Elham S. Darwish, Khalid A. Atia, and Ahmad M. Farag*

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

The versatile hitherto unreported 2-cyano-N-(4-{[(5-methylisoxazol-3-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-3-yl)amino]sulfonyl}phenyl)acetamide (18), 2-cyano-2-(1,3-dithian-2-ylidene)-N-4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide (19), and 2-cyano-N-(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.