Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold
Publication type: Journal Article
Publication date: 2018-02-15
scimago Q3
wos Q3
SJR: 0.321
CiteScore: 3.4
Impact factor: 1.9
ISSN: 00269247, 14344475
General Chemistry
Abstract
The electrochemically induced reaction of heterocyclic ketones and two equivalents of malononitrile in an undivided cell in alcohols in the presence of sodium bromide as mediator leading to the selective formation of substituted 6-heterospirocyclopropane-1,1,2,2-tetracarbonitriles in 50–75% yields as a result of the complex cascade process has been investigated. This new electrocatalytic cascade process smoothly proceeds with different types of heterocyclic ketones and resulted in ‘one-pot’ formation of 6-heterospirocyclopropane-1,1,2,2-tetracarbonitriles with prominent pharmacological and physiological activity. The application of this electrochemical cascade method to the formation of medicinally relevant substituted 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitriles is also beneficial from the viewpoint of diversity-oriented large-scale processes.
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Elinson M. N. et al. Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold // Monatshefte fur Chemie. 2018. Vol. 149. No. 6. pp. 1069-1074.
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Elinson M. N., Vereshchagin A. N., Korshunov A. D., Zaimovskaya T. A., Egorov M. P. Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold // Monatshefte fur Chemie. 2018. Vol. 149. No. 6. pp. 1069-1074.
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TY - JOUR
DO - 10.1007/s00706-018-2158-2
UR - https://doi.org/10.1007/s00706-018-2158-2
TI - Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold
T2 - Monatshefte fur Chemie
AU - Elinson, Michail N
AU - Vereshchagin, Anatoly N.
AU - Korshunov, Alexander D
AU - Zaimovskaya, Tatiana A
AU - Egorov, Mikhail P.
PY - 2018
DA - 2018/02/15
PB - Springer Nature
SP - 1069-1074
IS - 6
VL - 149
SN - 0026-9247
SN - 1434-4475
ER -
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@article{2018_Elinson,
author = {Michail N Elinson and Anatoly N. Vereshchagin and Alexander D Korshunov and Tatiana A Zaimovskaya and Mikhail P. Egorov},
title = {Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold},
journal = {Monatshefte fur Chemie},
year = {2018},
volume = {149},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s00706-018-2158-2},
number = {6},
pages = {1069--1074},
doi = {10.1007/s00706-018-2158-2}
}
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MLA
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Elinson, Michail N., et al. “Electrochemical cascade assembling of heterocyclic ketones and two molecules of malononitrile: facile and efficient ‘one-pot’ approach to 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile scaffold.” Monatshefte fur Chemie, vol. 149, no. 6, Feb. 2018, pp. 1069-1074. https://doi.org/10.1007/s00706-018-2158-2.
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