Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides

Abstract N -( Z )-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst- and solvent-free conditions at room temperature. The reacti...

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Bibliographic Details
Published in:Synlett 2012-09, Vol.23 (14), p.2069-2072
Main Authors: Trofimov, Boris A., Andriyankova, Ludmila V., Nikitina, Lina P., Belyaeva, Kseniya V., Mal’kina, Anastasiya G., Afonin, Andrei V., Ushakov, Igor A.
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
Free radicals chemistry
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
letter
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Abstract N -( Z )-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst- and solvent-free conditions at room temperature. The reaction proceeds via zwitterion–carbene intermediates which are trapped by isothiocyanates to form the zwitterion with ambident N–S anionic site, which then undergoes stereo- and regioselective migration of the alkenyl moiety.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290442