Synthesis and structure confirmation of 2,4-disubstituted thiazole and 2,3,4-trisubstituted thiazole as thiazolium bromide salts

Abstract

The synthesis of 4-substituted 2-(2-arylhydrazinyl)thiazol-3-ium bromides and 4-aryl-2-(substituted amino)-3-(phenylamino)thiazol-3-ium bromide derivatives in high yields from the interaction of mono-and di-substituted thiosemicarbazides with phenacyl bromide derivatives is reported. The synthesized products have been elucidated using various spectroscopic tools such as IR, NMR, and mass spectrometry. Also the structure of three of the obtained compounds have been confirmed using X-ray crystallographic analyses, which showed that compounds 2-[2-(2,4-dinitrophenyl)hydrazinyl]-4-phenylthiazol-3-ium bromide and 4-phenyl-2,3-bis(phenylamino)thiazol-3-ium bromide crystals have a monoclinic shape and belonged to space group P2 1 /c, whereas the crystals of 4-phenyl-2-(2-tosylhydrazinyl)thiazol-3-ium bromide show an orthorhombic shape with the space group Pbca

Convenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity

“…According to prior research and our own, 35,41,55 the interaction between thiosemicarbazides and phenacyl bromides is principally determined by the reaction conditions, substituted position, and solvent employed, as seen in Scheme 1. All obtained compounds were conrmed by X-ray crystallographic determination.…”

Visible-light-induced C–S bond formation in the synthesis of 2,4-disubstituted thiazoles through cascade difunctionalization of acetophenone: a greener approach

“…For instance, they exhibit properties akin to anti-inflammatory drugs like meloxicam, 16 anticancer drugs like dasatinib, 17,18 antiparasitic drugs like nitazoxanide, 19 pesticide drugs like thiabendazole, 20 antimicrobial drugs like sulfathiazole, 21 antifungal drugs like abafungin, 22,23 antineoplastic drugs like guineamide, 24,25 broad-spectrum third-generation cephalosporin antibiotics, 26 anti-bacterial drugs like cefotaxime, inhibitors like fatostatin, vitamin B 1 , thiamine, and antiulcerogenic drugs like famotidine. 27 Consequently, thiazole derivatives warrant thorough biological investigations to assess their potential applications in various pharmacological fields 28 (Fig. 1).…”

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

“…Thiazole derivatives are important in designing and discovering pharmaceuticals, and they are incorporated into the structures of antimicrobial (acinitrazole and sulfathiazole) [15], antidepressant (pexole) [16], antineoplastic (bleomycin) [17], anti-HIV (ritonavir) [18], antiasthmatic (cinalukast) [19], antiulcer (nizatidine) [20], antibiotic (penicillin), thiamine (vitamin B1) [21], non-steroidal immunomodulatory (fanetizole) [22], anti-inflammatory (anetizole, meloxicam, fentiazac), analgesic, antineoplastic (tiazofurin, dasatinib), antifungal (ravuconazole), antiparasitic (nitazoxanide), anti-inflammatory (anetizole, meloxicam, fentiazac), and antiulcer (nizatidine) [23,24] drugs and agents. Thiazoles possess a polyoxygenated phenyl molecule that showed anti-fungal activity [25] and thiazolium also possesses bis-thiazolium salts that have been screened as potent antimalarial agents.…”