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Abstract <p>The predominant tautomer form of 5-ethoxycarbonyl-substituted 1-hydroxyimidazoles (exhibiting antiviral activity towards orthopoxviruses) in a solution of aprotic DMSO-<i>d</i><sub>6</sub> has been elucidated from the data of <sup>1</sup>Н and <sup>13</sup>С NMR spectroscopy in comparison with model structures. The IR spectra (KBr pellets) have been considered. It has been shown that 1-hydroxyimidazoles <b>3а</b>, <b>3b</b> predominantly exist as <i>N</i>-hydroxy tautomers in the solution, forming crystal hydrates in the solid state, in which water favors the shift of the tautomeric equilibrium towards the <i>N</i>-oxide.</p>

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Investigation of Prototropic Tautomerism of Ethyl 2-Aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • E. I. Basanova,
  • T. Yu. Koldaeva,
  • V. P. Perevalov,
  • P. A. Nikitina

摘要

Abstract

The predominant tautomer form of 5-ethoxycarbonyl-substituted 1-hydroxyimidazoles (exhibiting antiviral activity towards orthopoxviruses) in a solution of aprotic DMSO-d6 has been elucidated from the data of 1Н and 13С NMR spectroscopy in comparison with model structures. The IR spectra (KBr pellets) have been considered. It has been shown that 1-hydroxyimidazoles 3а, 3b predominantly exist as N-hydroxy tautomers in the solution, forming crystal hydrates in the solid state, in which water favors the shift of the tautomeric equilibrium towards the N-oxide.