Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 9, Pages 1772-1777Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901397
Keywords
Nitrogen heterocycles; Electron-deficient compounds; Aldehydes; Multicomponent reactions; Alkynes
Categories
Funding
- Russian Fund for Basic Research [08-03-00156]
- Presidium of RAS [15]
- Presidium of Department of Chemical Sciences and Materials RAS [5.1]
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A novel three-component reaction between 1-substituted imidazoles, aldehydes, and electron-deficient acetylenes proceeds under mild conditions (20-25 degrees C, no catalyst, no solvent) to form an unknown family of C2-functionalized imidazoles in up to 74 % yield, the function constituting a push-pull combination of enol ether and acrylic moieties. In the case of cyanophenylacetylene, the function is built up stereospecifically to have the (Z) configuration. The interaction presumably occurs via zwitterion and carbene intermediates. The results contribute to basic imidazole and acetylene chemistry and open a shortcut to promising drug candidates.
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