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Synthesis of new cyanoethyl derivatives from 3-oxotriterpenoids

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Abstract

Reaction of 3-oxotriterpenoids and steroids with acrylonitrile in the presence of BnEt3NCl and 30% KOH in dioxane proceeds with the formation of 2,2-biscyanoethyl derivatives substituted in the α-position to 3-oxo group. In the presence of several α-hydrogen atoms at the 3-oxo group the reaction of cyanoethylation involved the positions C4 and C5, leading to 2,2,5-tricyanoethyl and 2,4-dicyanoethyl derivatives. The cyanoethylation of tetracyclic compounds occurred with the formation of monocyanoethyl derivatives with an overall increase in the yield.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    E. F. Khusnutdinova, А. V. Petrova, А. I. Poptsov, А. N. Lobov & I. E. Smirnova

  2. Bashkir State University, Ufa, Russia

    А. V. Petrova & О. S. Kukovinets

Authors
  1. E. F. Khusnutdinova
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  2. А. V. Petrova
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  3. А. I. Poptsov
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  4. А. N. Lobov
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  5. I. E. Smirnova
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  6. О. S. Kukovinets
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Corresponding author

Correspondence to E. F. Khusnutdinova.

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Original Russian Text © E.F. Khusnutdinova, А.V. Petrova, А.I. Poptsov, А.N. Lobov, I.E. Smirnova, О.S. Kukovinets, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1181–1188.

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Khusnutdinova, E.F., Petrova, А.V., Poptsov, А.I. et al. Synthesis of new cyanoethyl derivatives from 3-oxotriterpenoids. Russ J Org Chem 53, 1195–1203 (2017). https://doi.org/10.1134/S1070428017080073

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  • DOI: https://doi.org/10.1134/S1070428017080073

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