Three-component reaction between imidazoles, isocyanates, and cyanophenylacetylene: a short-cut to N-(Z)-alkenylimidazole-2-carboxamides

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 zwitte...

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Bibliographic Details
Published in:Tetrahedron letters 2012-12, Vol.53 (52), p.7040-7043
Main Authors: Belyaeva, Kseniya V., Andriyankova, Ludmila V., Nikitina, Lina P., Mal’kina, Anastasiya G., Afonin, Andrei V., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
Acetylene
Carbenes
Formations
Imidazole
Imidazoles
Isocyanates
Migration
Multicomponent reactions
Stereoselectivity
Tetrahedrons
Zwitterion/carbene intermediates
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.10.049