Published June 2018 | Version v1
Journal article

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

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

Description

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: .

Additional details

Identifiers

Publishing Information

Journal Title
Monatshefte fuer Chemie
Journal Volume
149
Journal Issue
6
Journal Page Range
p. 1069-1074
ISSN
0026-9247
CODEN
MOCHAP

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Copyright
Copyright (c) 2018 Springer-Verlag GmbH Austria, part of Springer Nature