The reaction of beta-amino-alpha,gamma-dicyanocrotononitrile with acetophenone: synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities.
Condensation of beta-amino-alpha,gamma-dicyanocrotononitrile (1) with acetophenone gave 2-amino-4-phenylpenta-1,3-diene-1,1,3-tricarbonitrile (2). The latter product was used in a series of heterocyclization reactions with different reagents such as diazonium salts, hydrazines, hydroxylamines and elemental sulfur to give pyridazine, pyrazole, isoxazole and thiophene derivatives, respectively. On the other hand, it gave pyridine derivatives with aromatic aldehydes folowed 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.
Mohareb
Rafat M
RM
Department of Chemistry, Cairo University, Giza, Egypt. raafat_mohareb@yahoo.com
El-Sharkawy
Karam A
KA
Sherif
Sherif M
SM
D000098:Acetophenones / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D009570:Nitriles / Q000737:chemistry; D011724:Pyridazines / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000098:Acetophenones; D000890:Anti-Infective Agents; D009570:Nitriles; D011724:Pyridazines; D011725:Pyridines; D013876:Thiophenes; C031103:crotononitrile; C038699:acetophenone