Utility of CyanoaceticAcid Hydrazide in Organic Synthesis: Synthesis and Characterization of Some Novel Heterocycles bearing 1,3,4-Oxadiazole Moeity | ||||
| Journal of Pharmaceutical and Applied Chemistry | ||||
| Volume 2, Issue 1, January 2016, Page 60-68 PDF (681.57 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.18576/jpac/030205 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
| Mounir A. A. Mohamed; Omar M. El-Hady; Ahmed M. El-Sayed | ||||
| Chemistry Department, Faculty of Science,Sohag University, Sohag, Egypt. | ||||
| Abstract | ||||
| 2,2'-(1,3,4-oxadiazole-2,5-diyl)diacetonitrile 2 has been prepared expeditiously from 2-cyano-N’-(2-cyanoacetyl)acetohydrazide1. Reaction of 2,2'-(1,3,4-oxadiazole-2,5-diyl)diacetonitrile 2 with aromatic aldehydes under mild alkaline conditions afforded the corresponding condensation products 3a-d, which in turn allowed to react with hydrazine, phenylhydrazine or hydroxylamine to give pyrazole and iosxazole derivatives (4-6)a-d. Also compound 3a-d was reacted with acetylacetone or ethyl acetoacetate to give pyran derivatives (7,8)a-d. Condensation of compound 2 with cyclopentanone afforded compound 9 which was reacted with acetylacetone or ethyl acetoacetate to give the corresponding spiropyran derivatives 10 and 11 respectively. The one-pot reaction of compound 2 with carbon disulfide or phenylisocyanate and ethyl chloroacetate under phase transfer catalysis conditions afforded the corresponding thiophene derivatives 12 and 13 respectively. Finally, the reaction of compound 2 with ethylcyanoacetate was studied carefully under non-catalytic and catalytic conditions where compounds 14-16 were obtained respectively. The antimicrobial activity of the obtained compounds was examined. The obtained products were characterised by their elemental and spectral data. | ||||
| Keywords | ||||
| Cyanoacetohydrazide; oxadiazole; cyanomethyl; spiro; PTC; antibacterial | ||||
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