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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

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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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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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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

    Michail N. Elinson, Anatoly N. Vereshchagin, Alexander D. Korshunov & Mikhail P. Egorov

  2. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation

    Tatiana A. Zaimovskaya

Authors
  1. Michail N. Elinson
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  2. Anatoly N. Vereshchagin
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  3. Alexander D. Korshunov
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  4. Tatiana A. Zaimovskaya
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  5. Mikhail P. Egorov
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Correspondence to Michail N. Elinson.

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Elinson, M.N., Vereshchagin, A.N., Korshunov, A.D. 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. Monatsh Chem 149, 1069–1074 (2018). https://doi.org/10.1007/s00706-018-2158-2

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  • DOI: https://doi.org/10.1007/s00706-018-2158-2

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