Amines (2) and (26) were obtained from the condensation of the corresponding amines with 3,4-difluoronitrobenzene. The reduction of nitro group produced the corresponding amines (3 and 27). The synthesis of esters (7, 12, 19, 28) was carried out from the treatment of the amines, (1, 3, 18, 27) with ethyl bromoacetate, then these compounds were converted to the corresponding hydrazides (8, 13, 29) by the treatment with hydrazine hydrate. The triazole was obtained from the intramolecular cyclisation of the corresponding carbothioamide in basic media and this compound was then converted to the morpholine-triazole-penicillin hybrid by a mannich reaction. The cyclocondensation of hydrazine carbothioamides (9b, 14, 21) or urea (4) with 2-bromo-1-(4-chlorophenyl)ethenone generated the thiazole derivatives. On the other hand, the treatment of 4, 9b, and 14 with ethyl bromoacetate yielded 4-oxo-1,3-thiazolidines (6, 11, 16). Three methods containing conventional, microwave, and ultrasound-mediated techniques were applied. Best results were assessed using microwave-and ultrasound-promoted procedures. The structures of the newly synthesised compounds were elucidated by spectroscopic techniques, and the antimicrobial activity screening studies were also performed. Some of them exhibited good to moderate activity on the test bacteria.
CITATION STYLE
Demirci, S. (2018). Synthesis of thiazole derivatives as antimicrobial agents by green chemistry techniques. Journal of the Turkish Chemical Society, Section A: Chemistry, 5(2), 393–414. https://doi.org/10.18596/jotcsa.375716
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