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. Khalifa^a, M. A. Amin^{a, b}, and M. A. N. Mosselhi^{a, c, #}

^#Phone: 00966543772635; e-mail: [email protected]

^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