SYNTHESIS AND OXIDATION OF ALL ISOMERIC 2-(PYRAZOLYL)ETHANOLS

Authors

  • Sergey P. Ivonin Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660
  • Eduard B. Rusanov Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660
  • Dmitriy M. Volochnyuk Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660 Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601

DOI:

https://doi.org/10.1007/5571

Keywords:

keto acids, pyrazoles, building blocks, oxidation, recyclization

Abstract

An efficient approach to the preparation of N-substituted 2-(pyrazol-4-yl)ethanols based on recyclization reaction of 3-(dimethoxymethyl)-2-methoxytetrahydrofuran with hydrazines is described. Oxidation by KMnO4 led to 2-(pyrazol-4-yl)-2-oxoacetic acids. In contrast, 2-(pyrazol-5-yl)ethanol under similar conditions gave only pyrazole-5-carboxylic acid, which formed as a result of oxidation followed by decarbonylation. 2-(Pyrazol-3-yl)ethanol in this oxidation reaction gave a mixture of 2-oxo-2-(pyrazol-3-yl)acetic acid and pyrazole-3-carboxylic acid.

Author Biography

Dmitriy M. Volochnyuk, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660 Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601

Biologically active compounds department, Head of the department

Downloads

Published

2020-04-01

Issue

Vol. 56 No. 3 (2020)

Section

Original Papers