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C2‐Functionalization of 1‐Substituted Imidazoles with Aldehydes and Electron‐Deficient Acetylenes: A Novel Three‐Component Reaction
Author(s) -
Trofimov Boris A.,
Andriyankova Ludmila V.,
Belyaeva Kseniya V.,
Mal'kina Anastasiya G.,
Nikitina Lina P.,
Afonin Andrei V.,
Ushakov Igor' A.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901397
Subject(s) - chemistry , zwitterion , surface modification , imidazole , acetylene , yield (engineering) , carbene , catalysis , enol , combinatorial chemistry , organic chemistry , medicinal chemistry , polymer chemistry , molecule , materials science , metallurgy
A novel three‐component reaction between 1‐substituted imidazoles, aldehydes, and electron‐deficient acetylenes proceeds under mild conditions (20–25 °C, no catalyst, no solvent) to form an unknown family of C2‐functionalized imidazoles in up to 74 % yield, the function constituting a push–pull combination of enol ether and acrylic moieties. In the case of cyanophenylacetylene, the function is built up stereospecifically to have the ( Z ) configuration. The interaction presumably occurs via zwitterion and carbene intermediates. The results contribute to basic imidazole and acetylene chemistry and open a shortcut to promising drug candidates.