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:... 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 Introduction privileged scaffolds tend to contain rigid heterocyclic system with predefined spatial orientation of functional In the last decades, the ideas and principles of ‘‘privileged groups for target recognition [3]. medicinal structures’’ [1, 2] have evolved to one of the Cyclopropane ring is considered as the main structural basic approaches for drug discovery search. Generally, the feature for lots of synthetic and naturally occurring com- pounds with inherent spectrum of biological activity such as enzyme inhibition or antibiotic, antitumor, antiviral, and & http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

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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Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer-Verlag GmbH Austria, part of Springer Nature
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-018-2158-2
Publisher site
See Article on Publisher Site

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 Introduction privileged scaffolds tend to contain rigid heterocyclic system with predefined spatial orientation of functional In the last decades, the ideas and principles of ‘‘privileged groups for target recognition [3]. medicinal structures’’ [1, 2] have evolved to one of the Cyclopropane ring is considered as the main structural basic approaches for drug discovery search. Generally, the feature for lots of synthetic and naturally occurring com- pounds with inherent spectrum of biological activity such as enzyme inhibition or antibiotic, antitumor, antiviral, and &

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Feb 15, 2018

References

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