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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 6, pp 1069–1074 | Cite as

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

  • Michail N. Elinson
  • Anatoly N. Vereshchagin
  • Alexander D. Korshunov
  • Tatiana A. Zaimovskaya
  • Mikhail P. Egorov
Original Paper
  • 41 Downloads

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.

Graphical abstract

Keywords

Electrochemical process Cascade reaction Heterocyclic ketones Malononitrile 6-Heterospiro[2.5]octane-1,1,2,2-tetracarbonitrile 6-Heterospirocyclopropane-1,1,2,2-tetracarbonitrile 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support of the Presidential Scholarship Program for State Support of Leading Science Schools of Russian Federation (Project no. 8012.2016.3).

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Michail N. Elinson
    • 1
  • Anatoly N. Vereshchagin
    • 1
  • Alexander D. Korshunov
    • 1
  • Tatiana A. Zaimovskaya
    • 2
  • Mikhail P. Egorov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. V. Topchiev Institute of Petrochemical SynthesisRussian Academy of SciencesMoscowRussian Federation

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