Synthesis and antimicrobial activity of 4-chloro-5-(2-nitrovinyl)-1H-imidazoles and products of their interaction with 3-methyl-2-pyrazolin-5-one

V. O. Chornous, O. Ya. Mel’nyk, A. M. Grozav, N. D. Yakovychuk, M. V. Vovk


The work is devoted to the synthesis of new derivatives of 5-(2-nitrovinyl)imidazole, investigation of their chemical behaviour in the Michael reaction with heterocyclic CH-acids and study of their antifungal and antibacterial action. It has been found that 1-substituted 4-chloro-5-(2-nitrovinyl)imidazoles can be prepared with 71-83% yields by heating 4-chloro-5-formylimidazoles with the excess of nitromethane or nitroethane in the presence of anhydrous ammonium acetate. The compounds synthesized are typical representatives of activated alkenes and react with 3-methyl-2-pyrazolin-5-one in the Michael reaction. It has been shown that when refluxing in water for 3 h the interaction proceeds regioselectively with the most nucleophilic C4 atom of pyrazolinone giving 4-[1-(4-chloro-1H-imidazole-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-oles. In the case of the spatially hindered exocyclic part of the molecule 1H NMR spectra have characteristic features. The biological screening results of the compounds obtained have confirmed a high bactericidal and fungicidal effect. It has been found that antimicrobial properties are dependent on the nature of the substituent in the position 1 of the imidazole cycle and the structure of the exocyclic fragment. In particular, the condensation products of 4-chloroimidazol-5-carbaldehyde with nitroethane showed 4-6 times higher bactericidal activity compared to the analogous compounds obtained from nitromethane.


4-chloro-5-formylimidazoles; nitroalkanes; 3-methyl-2-pyrazolin-5-one; 4-chloro-5-(2-nitrovinyl)imidazoles; 4-[1-(4-chloroimidazol-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-oles; antifungal and bactericidal activity


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