One pot synthesis of novel thiazolo[3,2-b][1,2,4]triazoles: A useful synthetic application of the acidified acetic acid method

Synthesis, characterization and evaluation of antibacterial activity of some thiazolo[3,2-b][1,2,4]triazole incorporating diphenylsulfone moieties☆

“…In the 1 H NMR spectra of thiazolotriazole, methyne proton appears as a singlet at 7.96-8.06 ppm, in agreement with data reported for analogous compounds [15,20,34], while the signal of the methylene proton (4.81-4.95 ppm) from compounds 4, 5 disappeared. The phenyl or p-phenylene protons from phenacyl or 4-bromophenacyl groups were seen at the expected chemical shifts and integral values (see Section 6).…”

“…These results are contrary to our expectations, but in concordance with other studies [15]. Moreover, similar MIC values obtained for 3c, 4c, 5c, 6c and 7c demonstrated again that the presence of condensed systems is not the main cause of appearance for antibacterial activity.…”

“…Thus, previous studies indicate that if cyclization take place in acidic media (H 2 SO 4 , H 3 PO 4 , HCl, CH 3 COOH) isomers [3,2-b] are obtained. However, if cyclization takes place in POCl 3 media, N-4 would be more basic owing to the formation of [2,3-c] isomers [15,19,20,30,31].…”

“…These condensed heterocyclic compounds can exist in both the isomer forms: thiazolo [3,2-b] [1,2,4]triazole and thiazolo [2,3-c] [1,2,4]triazole. Thiazolo [3,2-b] [1,2,4]-triazoles possess a broad spectrum of biological activities: antimicrobial [14][15][16], analgesic, anti-inflammatory [17][18][19][20], antipyretic [20], anticancer [21], vasodilatory [22].…”

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

“…The fusion of triazole and thiazole rings can lead to thiazolotriazoles with superior biological properties due to mutual influence of the pharmacophores centers present in the molecule. Thus, literature data indicate that numerous thiazolo [3,2-b] [1,2,4] triazoles derivatives have been reported to possess antibacterial, [3][4][5][6][7][8][9] antifungal, 3,[6][7][8][9] anti-inflammatory, 3,10,11) analgesic, 3,10) antiproliferative, 12) anticonvulsant 13) properties. Also, thiazolo [3,2-b][1,2,4] triazol-ones have been studied for their properties with respect to their biological activities including anti-inflammatory, [14][15][16][17] analgesic, 15,17) anticancer, [18][19][20] antibacterial, 21) antifungal 21) and anticonvulsant.…”