Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity

Abstract

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.

An Approach to Polysubstituted Triazipines, Thiadiazoles and Thiazoles Based on Benzopyran Moiety Through The Utility of Versatile Hydrazonoyl Halides as In Vitro Monoamine Oxidase Inhibitors

“…Hydrazonoyl halides are quite reactive reagents, which could react with different functional groups such as thiol, amino, NH, and active methylene groups. Examples for the ring systems that have been synthesized from hydrazonoyl halides are pyrazoles, thiazoles , imidazoles , triazoles , thiadiazoles , and tetrazines . On the other hand, the benzopyran moiety is an important heterocyclic structure in synthetic and biological applications , also, benzopyrans posses a quite inhibitory activity against monoamine oxidase .…”