Synthesis of new cyanoethyl derivatives from 3-oxotriterpenoids

Reaction of 3-oxotriterpenoids and steroids with acrylonitrile in the presence of BnEt 3 NCl 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 o...

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Published in:Russian journal of organic chemistry 2017-08, Vol.53 (8), p.1195-1203
Main Authors: Khusnutdinova, E. F., Petrova, А. V., Poptsov, А. I., Lobov, А. N., Smirnova, I. E., Kukovinets, О. S.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Cyanoethylation
Derivatives
Hydrogen atoms
Organic Chemistry
Steroids
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description Reaction of 3-oxotriterpenoids and steroids with acrylonitrile in the presence of BnEt 3 NCl 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 C 4 and C 5 , 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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subjects Chemical synthesis
Chemistry
Chemistry and Materials Science
Cyanoethylation
Derivatives
Hydrogen atoms
Organic Chemistry
Steroids
title Synthesis of new cyanoethyl derivatives from 3-oxotriterpenoids
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