C2‐Functionalization of 1‐Substituted Imidazoles with Aldehydes and Electron‐Deficient Acetylenes: A Novel Three‐Component Reaction | Zendy

Trofimov Boris A. | Zendy; Andriyankova Ludmila V. | Zendy; Belyaeva Kseniya V. | Zendy; Mal'kina Anastasiya G. | Zendy; Nikitina Lina P. | Zendy; Afonin Andrei V. | Zendy; Ushakov Igor' A. | Zendy

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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.

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