Acta Pharm. 58 (2008) 429-444
Original research paper
The reaction
of β-amino-α,γ-dicyanocrotononitrile
with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives
with antimicrobial activities
RAFAT M.
MOHAREB, KARAM A. El-SHARKAWY and SHERIF M. SHERIF
raafat_mohareb@yahoo.com
Department of
Chemistry, Faculty of Science,
Department of Organic
Chemistry, Faculty of Pharmacy,
Accepted November 11, 2008
Condensation of β-amino-α,γ-dicyanocrotononitrile (1) with acetophenone gave the 2-amino-4-phenylpenta-1,3-diene-1,1,3-tricarbonitrile (2). The latter product was used in a series of heterocyclization reactions when react with different reagents like diazonium salts, hydrazines, hydroxylamine and elemental sulfur to give pyridazine, pyrazole, isoxazole and thiophene derivatives, respectively. On the other hand, it gave pyridine derivatives with aromatic aldehydes followed by reaction with cyanomethylene reagents. The MIC values for the newly synthesized product were measured against E. coli, B. cereus, B. subtilis and C. albicans.
Keywords: pyridine, isoxazole, pyridazine, thiophene, antimicrobial
activity