Collect. Czech. Chem. Commun. 1984, 49, 1342-1353

The possibilities of polarography in the chemistry of nitroazoles

Dragica Dumanovića, Janka Ćirića, Djuro Kosanovića and Dragoslav Jeremićb

a Galenika Pharmaceutical and Chemical Industry Institute, Belgrade 110 00, Yugoslavia
b Faculty of Sciences, University of Belgrade, Belgrade 110 00, Yugoslavia


Based on systematic investigation of mononitroimidazoles, selective polarographic and spectrophotometric methods for determination of nitrazole compounds in reaction mixture are proposed. It was proved that the selectivity is based on the different properties of the nitro group due to the effects of the nitro group position in the ring, the type and position of the other substituents and on the fact whether the compound is N-substituted or not. The proposed methods can be successfully used for monitoring the synthetic procedures and decreasing the number of experiments for optimization. Based on the anticipated and proved behaviour of the nitro compounds of pyrazole, novel mononitropyrazole derivatives were synthetized in a new way and with high yields. Applying the polarographic method it was discovered that during N-substitution of tautomeric mononitroimidazole and mononitropyrazole substrates other byproducts were obtained besides the main products and undesired isomers. The products were identified and then a correct and more complete N-substitution scheme could be given. Following quantitatively these N-substitution processes conclusions which directly concern the mechanism of reactions were drawn.