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Short Paper | Regular issue | Vol 83, No. 8, 2011, pp.1873-1888
Published online, 25th May, 2011
DOI: 10.3987/COM-11-12240
■ Annulation and Evaluation of Antibacterial Activity of the New Fused Tricyclic (5,5,6) Ring System of Pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines

Kamal F. M. Atta,* Mohamed G. Marei, Somia M. Abd El-Magiad, and Faten H. A. El-Nashar

*Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt

Abstract

A series of the new fused 5-aryl-8-phenyl-2H-pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidine-3-thiones 2 were prepared in excellent yields by the reaction of 5-aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 with carbon disulfide in the presence of potassium hydroxide. The pyrazolotriazolopyrimidinethiones gave with certain electrophiles the respective 6-substituted 3-thiones 4-6 rather than the 7-substituted isomeric structure 7. Oxidation of 2 with sodium nitrite or benzenediazonuim chloride afforded the corresponding disulfides 9 or 10 respectively. Moreover, the pyrazolotriazolopyrimidinones 8 were prepared upon reaction with alkaline hydrogen peroxide. All the above compounds were evaluated as antibacterial agents against a variety of microorganisms.