Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4 H-chromene)-4,3′-oxindole system

An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4 H-ch...

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Bibliographic Details
Published in:Tetrahedron 2007-10, Vol.63 (42), p.10543-10548
Main Authors: Elinson, Michail N., Ilovaisky, Alexey I., Dorofeev, Alexander S., Merkulova, Valentina M., Stepanov, Nikita O., Miloserdov, Fedor M., Ogibin, Yuri N., Nikishin, Gennady I.
Format: Article
Language:English
Subjects:
Chromenes
Electrocatalysis
Electrochemistry
Multicomponent reactions
Spirooxindoles
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Summary:An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4 H-chromene system in 83–98% yields. The application of this efficient electrocatalytic method to the formation of medicinally relevant spirocyclic (4 H-chromene)-4,3′-oxindoles is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel, facile, and environmentally benign synthetic concept for multicomponent reaction strategy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.07.080