1415219-01-0Relevant 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.