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
Creators
- 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
INIS
- Country of Publication
- Austria
- Country of Input or Organization
- Austria
- INIS RN
- 50008744
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; S77: NANOSCIENCE AND NANOTECHNOLOGY;
- Descriptors DEI
- ALCOHOLS; ELECTROCHEMISTRY; KETONES; MOLECULES; OCTANE; SODIUM BROMIDES
- Descriptors DEC
- ALKALI METAL COMPOUNDS; ALKANES; BROMIDES; BROMINE COMPOUNDS; CHEMISTRY; HALIDES; HALOGEN COMPOUNDS; HYDROCARBONS; HYDROXY COMPOUNDS; ORGANIC COMPOUNDS; SODIUM COMPOUNDS; SODIUM HALIDES
Optional Information
- Copyright
- Copyright (c) 2018 Springer-Verlag GmbH Austria, part of Springer Nature