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Molecules 2015, 20(10), 18201-18218; doi:10.3390/molecules201018201

Synthesis of Some Novel Heterocyclic and Schiff Base Derivatives as Antimicrobial Agents

1
Department of Chemistry, Faculty of Science, University of Ain Shams, Cairo 11566, Egypt
2
Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
3
Applied Organic Chemistry Department, National Research Center, Dokki, Cairo 12622, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 5 September 2015 / Revised: 20 September 2015 / Accepted: 23 September 2015 / Published: 7 October 2015
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [864 KB, uploaded 7 October 2015]   |  

Abstract

Treatment of 2,3-diaryloxirane-2,3-dicarbonitriles 1ac with different nitrogen nucleophiles, e.g., hydrazine, methyl hydrazine, phenyl hydrazine, hydroxylamine, thiosemicarbazide, and/or 2-amino-5-phenyl-1,3,4-thiadiazole, afforded pyrazole, isoxazole, pyrrolotriazine, imidazolothiadiazole derivatives 25, respectively. Reacting pyrazoles 2ac with aromatic aldehydes and/or methyl glycinate produced Schiff’s bases 7ad and pyrazolo[3,4-b]-pyrazinone derivative 8, respectively. Treating 7 with ammonium acetate and/or hydrazine hydrate, furnished the imidazolopyrazole and pyrazolotriazine derivatives 9 and 10, respectively. Reaction of 8 with chloroacetic acid and/or diethyl malonate gave tricyclic compound 11 and triketone 12, respectively. On the other hand, compound 1 was reacted with active methylene precursors, e.g., acetylacetone and/or cyclopentanone producing adducts 14a,b which upon fusion with ammonium acetate furnished the 3-pyridone derivatives 15a,b, respectively. Some of newly synthesized compounds were screened for activity against bacterial and fungal strains and most of the newly synthesized compounds showed high antimicrobial activities. The structures of the new compounds were elucidated using IR, 1H-NMR, 13C-NMR and mass spectroscopy. View Full-Text
Keywords: oxirane; pyrazole; isoxazole; pyrazolopyrazine; Schiff bases; pyridones; antimicrobial activities oxirane; pyrazole; isoxazole; pyrazolopyrazine; Schiff bases; pyridones; antimicrobial activities
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Azab, M.E.; Rizk, S.A.; Amr, A.E.-G. Synthesis of Some Novel Heterocyclic and Schiff Base Derivatives as Antimicrobial Agents. Molecules 2015, 20, 18201-18218.

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