Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles
2015
Nikitina, Polina A. | Peregudov, Aleksandr S. | Koldaeva, Tatiana Yu | Kuz'mina, Ludmila G. | Adiulin, Evgeniy I. | Tkach, Iosif I. | Perevalov, Valery P.
Novel 2-(2-hydroxyphenyl) substituted imidazoles have been synthesized. A prototropic tautomerism of the 1-hydroxyimidazole derivatives has been studied. X-ray diffraction analysis and IR-spectroscopy have revealed that in the solid state the title compounds exist as the N-hydroxy tautomers. The 1H and 13C NMR spectra of the new imidazole derivatives are discussed. It has been shown that in chloroform solutions 5-carbonyl substituted 2-(2-hydroxyphenyl)-1-hydroxyimidazoles exist in the N-hydroxy tautomeric form. A transition to DMSO results in the existence of the 1-hydroxyimidazoles under study as the N-oxide tautomers.
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