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α,α‐Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol‐2‐yl hydrazonobutanoates, thiazol‐2‐yl pyrazole‐4‐carboxylates and acids
Author(s) -
Kiran Vijay,
Joshi Radhika,
Pundeer Rashmi
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3937
Subject(s) - chemistry , pyrazole , thiazole , bacillus subtilis , candida albicans , hydrolysis , escherichia coli , staphylococcus aureus , antibacterial activity , bacteria , organic chemistry , microbiology and biotechnology , biochemistry , genetics , gene , biology
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)‐1 H ‐pyrazole‐4‐carbxylates, basic hydrolysis of which gives the corresponding acids, 3‐methyl‐1‐(4‐arylthiazol‐2‐yl)‐1 H ‐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 .