B. Trofimov, L. V. Andriyankova, L. Nikitina
Sep 1, 2012
Citations
0
Influential Citations
13
Citations
Journal
Synlett
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.