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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

Abstract Treatment of 2,3-diaryloxirane-2,3-dicarbonitriles 1a–c 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 2–5, respectively. Reacting pyrazoles 2a–c with aromatic aldehydes and-or methyl glycinate produced Schiff’s bases 7a–d and pyrazolo3,4-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





Autor: Mohamed E. Azab 1,* , Sameh A. Rizk 1 and Abd El-Galil E. Amr 2,3

Fuente: http://mdpi.com/



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