Antioxidant and Antimicrobial Activities of Some New Synthesized Triazole, Thiazolone, and Thiazine Containing Fused Rings of Imidazopyridine

Abstract

Several heterocyclic compounds bearing an imidazo(1,2a)pyridine moiety have been synthesized in this work, including triazole, thiazol, and thiazolone. This was done by condensation of 2-aminopyridine with 2-aminopyridine with 4-bromophencyl bromide or 4-phenylphencyl bromide to produce 2-substituted phenyl imidazo(1,2a)pyridine compounds 1 and 2. The Vilsmeier-Haak reaction was used to create the aldehyde group at position 3 of the 2-substituted phenyl imidazo(1,2a)pyridine ring (3 and 4). The reaction of compounds 3 and 4 with thiosemicarbazide afforded thiosemicarbazone derivatives 5 and 6 in 66 and 70% yields, respectively. These derivatives (5 and 6) were then subjected to three different cyclization reactions to obtain 1,3-thiazolone (7 and 8), 1,2,4-triazole (9 and 10), and 1,3-thiazole (11 and 12) derivatives. The FT-IR spectroscopy was used to confirm the structure of these derivatives, and the 1H NMR spectroscopy was used for some of them. A few of the produced compounds were examined for antimicrobial and antioxidant activities