FEATURES OF THE REACTION OF 5-AMINOISOXAZOLES WITH DIETHYL 2-OXOSUCCINATE. SYNTHESIS OF ETHYL 6-HYDROXYISOXAZOLO[5,4-<i>b</i>]PYRIDINE-4-CARBOXYLATES

Authors

  • Валерий С. Толкунов L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkivske Shose 50, Kyiv 02160
  • Андрей С. Толкунов L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkivske Shose 50, Kyiv 02160
  • Ольга В. Смирнова L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkivske Shose 50, Kyiv 02160
  • Сергей В. Толкунов L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkivske Shose 50, Kyiv 02160

DOI:

https://doi.org/10.1007/6767

Keywords:

5-aminoisoxazoles, diethyl 2-oxosuccinate, ethyl 6-hydroxyisoxazolo[5, 4-b]pyridine-4-carboxylates, trifluoroacetic acid

Abstract

Condensation of 5-aminoisoxazoles bearing substituents at position 3 with diethyl 2-oxosuccinate sodium salt in trifluoroacetic acid proceeded with the formation of diethyl (Z)-2-(5-amino-3-methylisoxazol-4-yl)but-2-enedioates. Cyclization of the latter in the presence of sodium ethoxide in alcohol provided ethyl 6-hydroxyisoxazolo[5,4-b]pyridine-4-carboxylates. Ester hydrolysis gave the respective 6-hydroxyisoxazolo[5,4-b]pyridine-4-carboxylic acids.

Authors: Valery S. Tolkunov*, Andrew S. Tolkunov, Olga V. Smirnova, Sergei V. Tolkunov

Author Biography

Валерий С. Толкунов, L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkivske Shose 50, Kyiv 02160

отдел химии гетероциклических соединений, канд.хим.наук, с.н.с.

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Published

2022-09-21

Issue

Vol. 58 No. 8/9 (2022)

Section

Original Papers