- 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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- Electrochemical transformation of malononitrile and ketones into 3,3-disubstituted-1,1,2,2-tetracyanocyclopropanes
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Electrolysis of malononitrile in the presence of ketones and NaBr in ethanol in undivided cell results in formation of 3,3-disubstituted-1,1,2,2-tetracyanocyclopropanes
- Nikishin,Elinson,Lizunova,Ugrak
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- One-pot cascade assembling of 3-substituted tetracyanocyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action
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The new cascade reaction was found: the formation of cyclopropanes from alkylidenemalononitriles and malononitrile by the only bromine direct action; the action of aqueous bromine on the equal amounts of alkylidenemalononitriles and malononitrile in EtOH-
- Vereshchagin, Anatolii N.,Elinson, Michail N.,Stepanov, Nikita O.,Nikishin, Gennady I.
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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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- Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirobicyclic and spirotricyclic compounds containing 1,1,2,2-tetracyanocyclopropane fragment
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Electrolysis of malononitrile and cycloalkylidenemalononitriles in EtOH in an undivided cell in the presence of NaBr affords spirobicyclic compounds containing a 1,1,2,2-tetracyanocyclopropane fragment in 50-88% yields.
- Elinson,Fedukovich,Vereshchagin,Dorofeev,Dmitriev,Nikishin
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p. 2235 - 2240
(2007/10/03)
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- Cyclopropanation of Electron-deficient Alkenes and Wideqvist-type Synthesis of Cyclopropanes mediated by Indium Metal
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Cyclopropanation of electron-deficient alkenes and Wideqvist-type transformation of carbonyl compounds to cyclopropanes have been achieved by the action of active methylene dibromides and metallic indium.
- Araki, Shuki,Butsugan, Yasuo
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p. 1286 - 1287
(2007/10/02)
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