Synthesis of Nitrones Based on Triterpenes C<sup>3</i>-Hydroxylamines of the Lupane Series

An approach was developed to the synthesis of triterpene C3-nitrones containing the amide function at C28-position, new derivatives of pentacyclic triterpenoids of the lupan series. Diastereomeric triterpene 3β- and 3α-hydroxylamines obtained by reduction of oxime based on betulonic acid isopropylamide with NaBH3CN in a solution of 2 M HCl in MeOH were used as starting compounds. Nitrones were synthesized by condensation of hydroxylamines with substituted benzaldehydes in dichloromethane in the presence of Na2SO4.

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Journal
Журнал Общей Химии
Published
2024-12-20
DOI
https://doi.org/10.31857/s0044460x24070022
Citations
1
Primary Topic
Natural product bioactivities and synthesis
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article
Field-Weighted Citation Impact
0.23
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article

Synthesis of Nitrones Based on Triterpenes C3</i>-Hydroxylamines of the Lupane Series

Л. В. Спирихин, N. G. Komissarova, A. V. Orlov
1 citations
Журнал Общей Химии
Natural product bioactivities and synthesis
0.23
article

Synthesis of Nitrones Based on Triterpenes C3</i>-Hydroxylamines of the Lupane Series

Л. В. Спирихин, N. G. Komissarova, A. V. Orlov
article en
1 citations

Abstract

An approach was developed to the synthesis of triterpene C3-nitrones containing the amide function at C28-position, new derivatives of pentacyclic triterpenoids of the lupan series. Diastereomeric triterpene 3β- and 3α-hydroxylamines obtained by reduction of oxime based on betulonic acid isopropylamide with NaBH3CN in a solution of 2 M HCl in MeOH were used as starting compounds. Nitrones were synthesized by condensation of hydroxylamines with substituted benzaldehydes in dichloromethane in the presence of Na2SO4.

Журнал Общей ХимииVol. 94(7)
Ufa Institute of Chemistry (RU)
Openalex Percentile: Top 40%
Natural product bioactivities and synthesis
0.23
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