- Synthesis of 3-Arylcyclopropane-1,1,2,2-tetracarbonitriles under Micellar Catalysis
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An environmentally benign procedure has been developed for the synthesis of 3-arylcyclopropane- 1,1,2,2-tetracarbonitriles in an aqueous surfactant solution.
- Bardasov,Alekseeva, A. Yu.,Bezgin,Ershov
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p. 1839 - 1841
(2019/03/26)
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- A new type of cascade reaction: direct conversion of carbonyl compounds and malononitrile into substituted tetracyanocyclopropanes
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A new type of chemical cascade reaction was found: the direct formation of cyclopropanes from carbonyl compounds and C-H acid. The action of free halogen or active halogen containing compounds on a mixture of 1 equiv of carbonyl compound and 2 equiv of malononitrile in a basic alcohol solution results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 15-80% yield. The latter are well-known precursors for the different bicyclic heterosystems, among them compounds containing a cyclopropane ring and possessing different types of pharmacological activity. Thus, the new, simple and efficient 'one-pot' way to substituted tetracyanocyclopropanes in 50-80% yield was found directly from such simple and reasonable starting compounds as aldehydes, or some cyclic ketones, or substituted cyclohexanones and malononitrile.
- Elinson, Michail N.,Vereshchagin, Anatolii N.,Stepanov, Nikita O.,Ilovaisky, Alexey I.,Vorontsov, Alexander Ya.,Nikishin, Gennady I.
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experimental part
p. 6057 - 6062
(2011/03/19)
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- A new strategy of the chemical route to the cyclopropane structure: direct transformation of benzylidenemalononitriles and malononitrile into 1,1,2,2-tetracyanocyclopropanes
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The new reaction was found: the direct formation of cyclopropanes from activated olefins and C-H acids. The action of free halogen or active halogen containing compounds on the equal amounts of benzylidenemalononitriles and malononitrile in basic alcohol
- Elinson, Michail N.,Feducovich, Sergey K.,Stepanov, Nikita O.,Vereshchagin, Anatolii N.,Nikishin, Gennady I.
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p. 708 - 713
(2008/09/16)
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- Electrochemical transformation of malononitrile and carbonyl compounds into functionally substituted cyclopropanes: Electrocatalytic variant of the Wideqvist reaction
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Electrolysis of malononitrile and carbonyl compounds in the presence of alkali metal halides in an undivided cell results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 60-90% yield. This electrocatalytic variant of the Wideqvist reaction using malononitrile instead of bromomalonitrile was successfully performed. Electrocatalytic transformation of substituted 1,1,2,2-tetracyanocyclopropanes in methanol or ethanol in an undivided cell leads to substituted 2-amino-4,4-dialkoxy-1,5- dicyano-3-azabicyclo[3.1.0]hex-2-enes in 70-95% yields after 0.05-0.10 F/mol of electricity has been passed. (C) 2000 Elsevier Science Ltd.
- Elinson, Michail N.,Feducovich, Sergey K.,Lizunova, Tatiana L.,Nikishin, Gennady I.
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p. 3063 - 3069
(2007/10/03)
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