Synthesis and study of prototropic tautomerism of 2-(2-hydroxyphenyl)-1-hydroxyimidazoles

• Published in: Tetrahedron Vol. 71; no. 33; pp. 5217 - 5228
• Main Authors: Nikitina, Polina A., Peregudov, Aleksandr S., Koldaeva, Tatiana Yu, Kuz'mina, Ludmila G., Adiulin, Evgeniy I., Tkach, Iosif I., Perevalov, Valery P.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.08.2015; Elsevier
• Subjects: 1-Hydroxyimidazole; Chemistry; Chemistry, Organic; Imidazole N-oxide; IR spectroscopy; NMR spectroscopy; Physical Sciences; Prototropic tautomerism; Science & Technology; X-ray diffraction; BYFRGBYXIBBJOB-UHFFFAOYSA-N; YDWIRPWFJBMAKY-UHFFFAOYSA-N; SXFYTSNZHJFBRU-UHFFFAOYSA-N; OTINAJGDCSHHLI-UHFFFAOYSA-N; SNZUTVWENQERIC-UHFFFAOYSA-N; X-ray diffraction; BPTUSQVXSMTFCL-UHFFFAOYSA-N; GARJUHYAEZYJQU-UHFFFAOYSA-N; ADZUEQDGUIXQJF-UHFFFAOYSA-N; PMIZGMGYDLFILF-UHFFFAOYSA-N; DYIJPZIGHVAEGG-UHFFFAOYSA-N; RZEIOKRPWFSMRS-UHFFFAOYSA-N; Imidazole N-oxide; 1-Hydroxyimidazole; JXFFFDXBCFBBJG-UHFFFAOYSA-N; YDNYUMXVQLSPOU-UHFFFAOYSA-N; BEWYPNNGKQVKBI-UHFFFAOYSA-N; VGEBTADZDYVWJY-UHFFFAOYSA-N; Prototropic tautomerism; HMZSWHARANQXHD-UHFFFAOYSA-N; IR spectroscopy; CQNYYCWMGRITQE-UHFFFAOYSA-N; BMUSQXAYGGMSDJ-UHFFFAOYSA-N; CDLWDZSCUFULST-UHFFFAOYSA-N; NMR spectroscopy; DZUSWEWCOWGYTB-UHFFFAOYSA-N; ZSJSBCIPCQQNRC-UHFFFAOYSA-N; XDWIRYVNPSRZAI-UHFFFAOYSA-N; COMPLEXES; HYDROXYIMIDAZOLE; ZINC(II); 5-MEMBERED RINGS; HETEROCYCLES; IMIDAZOLE; N-OXIDE DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2015.06.032

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. [Display omitted]