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

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 Full article

Journal

Monatshefte Fur Chemie
ISSN: 1434-4475 , E-ISSN: 0026-9247

Output data

Year: 2018, Volume: 149, Number: 6, Pages: 1069-1074 Pages count : 6 DOI: 10.1007/s00706-018-2158-2

Authors

Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹ , Korshunov Alexander D. ¹ , Zaimovskaya Tatiana A. ² , Egorov Mikhail P. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation

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.

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. V.149. N6. P.1069-1074. DOI: 10.1007/s00706-018-2158-2 WOS Scopus OpenAlex

Web of science:	WOS:000433333300009
Scopus:	2-s2.0-85042074171
OpenAlex:	W2794197651

DB	Citing
OpenAlex	5
Scopus	6
Web of science	8