Site Selectivity in Reactions of Hydrazonoyl Halides with Heterocycles Containing Amine and Thione Groups Leading to Fused Heterocycles of Potential Antimicrobial Activity
M. E. A. Khalifaa, M. A. Amina, b, and M. A. N. Mosselhia, c, #
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a Department of Chemistry, Faculty of Science, Taif University, P.O. 888, Taif, Saudi Arabia; b Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt; c Department of Chemistry, Faculty of Science, Cairo University, 12613-Giza, Egypt
Received April 25, 2013; in final form June 20, 2013
Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures of the newly synthesized compounds were elucidated by chemical evidence and their IR, 1H, 13C NMR, and MS spectra. Furthermore, some of the products were screened against different strains of bacteria and fungi.
Keywords: hydrazonoyl halide, site-selectivity, quinazoline, pyrimidine, antimicrobial activity.
Биоорг. химия 2014, 40 (1): 117-124