1079368-40-3Relevant articles and documents
Three-component reaction between imidazoles, isocyanates, and cyanophenylacetylene: A short-cut to N-(Z)-alkenylimidazole-2-carboxamides
Belyaeva, Kseniya V.,Andriyankova, Ludmila V.,Nikitina, Lina P.,Mal'Kina, Anastasiya G.,Afonin, Andrei V.,Trofimov, Boris A.
supporting information, p. 7040 - 7043 (2013/01/15)
1-Substituted imidazoles, isocyanates, and cyanophenylacetylene react under mild (rt), non-catalytic solvent-free conditions to give (Z)-(2-cyano-1- phenylethenyl)imidazole-2-carboxamides in up to 72% yields and with ca. 100% stereoselectivity. The reaction starts from the initial formation of zwitterion/carbene intermediates captured by the isocyanate as the electrophile followed by migration of the alkenyl moiety from the N-3 atom to the anionic center at the carboxamide nitrogen. Thus, the reaction provides an easy access to a novel family of functionalized imidazoles.
Stereoselective C(2)-vinylation of 1-substituted imidazoles with 3-phenyl-2-propynenitrile
Trofimov, Boris A.,Andriyankova, Lyudmila V.,Belyaeva, Kseniya V.,Mal'kina, Anastasiya G.,Nikitina, Lina P.,Afonin, Andrei V.,Ushakov, Igor A.
experimental part, p. 9155 - 9157 (2009/04/04)
(Chemical Equation Presented) First examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus are described. 1-Substituted imidazoles 1a-e are C(2)-vinylated with 3-phenyl-2-propynenitrile (2) at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles 3a-e, mainly (c.a. 95%) as (Z)-isomers, in 56-88% yield. The reaction is likely to involve the zwitterionic intermediates, which prototropically isomerizes to imidazole carbene and eventually undergoes the selective 3,2-shift of the functionalized vinyl substituent.
