117481-01-3Relevant academic research and scientific papers
α,α-Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol-2-yl hydrazonobutanoates, thiazol-2-yl pyrazole-4-carboxylates and acids
Joshi, Radhika,Kiran, Vijay,Pundeer, Rashmi
, (2020)
In the present study, α,α-dibromoacetophenones are used as efficient precursors for the facile synthesis of several new hydrazonothiazoles, ethyl 3-((4-arylthiazol-2-yl)hydrazono)butanoates, which undergo Vilsmeier-Haack cyclization to obtain thiazolylpyrazole esters, ethyl 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylates, basic hydrolysis of which gives the corresponding acids, 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylic acids. All these compounds are tested for antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis; Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa and antifungal activity against Saccharomyces cerevisiae and Candida albicans.
Reaction of 4-Aryl-2-hydrazinothiazoles with Ethyl Acetoacetate: A Reinvestigation
Singh, S. P.,Sehgal, Subhash,Diwakar, P.,Vaid, R. K.
, p. 573 - 575 (2007/10/02)
The reaction of 4-aryl-2-hydrazinothiazoles (1a,b) with ethyl acetoacetate (2) affords 1-(4'-aryl 2'-thiazolyl)-3-methylpyrazol-5-ols (3a,b) rather than 3-arylthiazolotriazepin-5-ones (4a,b),as previously reported.The correct structural assignment is based on an alternate synthesis involving reaction of phenacyl bromides (6) and 3-methylpyrazol-5-ol-1-thiocarboxamide (7).The keto/enol tautomerism of 3 has been investigated using PMR spectroscopy.
