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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis and antimicrobial activity of some new heterocycles incorporating antipyrine moiety
Samir Bondock1, Ramy Rabie, Hassan A Etman
1Department of Chemistry, Faculty of Science, Mansoura University, El-gomhuria Street, ET-35516 Mansoura, Egypt. Bondock@mans.edu.eg
Abstract:
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.
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