Synthesis and antimicrobial activity of some new heterocycles incorporating antipyrine moiety.
2-cyano-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide (1) was utilized as key intermediate for the synthesis of some new coumarin 2, pyridine 3, pyrrole 4, thiazole 7, pyrido[2',3':3,4][pyrazolo[5,1-c]triazine and aminopyrazole 9. Treatment of aminopyrazole 9 with nitrous acid, 1,3-dicarbonyl compounds, enaminone, and DMF-DMA led to the formation of pyrazolo[3,4-d]triazine 10, pyrazolo[1,5-a]pyrimidines 11, 12, 14, and pyrazolo[3,4-d]pyrimidine 13, respectively. Condensation of 9 with isatin afforded Schiff base 16. The newly synthesized compounds were characterized by IR, 1H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.
Bondock
Samir
S
Department of Chemistry, Faculty of Science, Mansoura University, El-gomhuria Street, ET-35516 Mansoura, Egypt. Bondock@mans.edu.eg
Rabie
Ramy
R
Etman
Hassan A
HA
Fadda
Ahmed A
AA
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000983:Antipyrine / Q000737:chemistry*; D001419:Bacteria / Q000187:drug effects; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009570:Nitriles / Q000737:chemistry
D000890:Anti-Infective Agents; D006571:Heterocyclic Compounds; D009570:Nitriles; D000983:Antipyrine; C031594:2-cyanoacetamide