Synthesis of Thiazole Derivatives as Antimicrobial Agents by Green Chemistry Techniques

Year 2018, Volume: 5 Issue: 2, 393 - 414, 01.01.2018

Serpil Demirci

https://doi.org/10.18596/jotcsa.375716

Cited By: 9

Abstract

Amine (2) and (26)
was 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
ethylbromoacetate, then these compounds were converted to the corresponding
hydrazides (8, 13, 29) by the treatment with hydrazine hydrate. Triazole was
obtained from the intramolecular cyclisation of the corresponding carbothioamide
in basic media and this compound wad 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 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 ultrasounds promoted procedures. All the newly
synthesized compounds were characterized on the basis of spectroscopic
techniques, and they were screened for their antimicrobial activity. Some of
them exhibited good-moderate activity on the test bacteria.

Keywords

Antimicrobial activity, microwave, imidazole, morpholine, green chemistry

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