C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction
Тип публикации: Journal Article
Дата публикации: 2010-03-01
scimago Q2
wos Q2
БС2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
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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Trofimov B. A. et al. C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction // European Journal of Organic Chemistry. 2010. Vol. 2010. No. 9. pp. 1772-1777.
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Trofimov B. A., Andriyankova L. V., Belyaeva K. V., Mal’kina A. G., Nikitina L. P., Afonin A., Ushakov I. C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction // European Journal of Organic Chemistry. 2010. Vol. 2010. No. 9. pp. 1772-1777.
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TY - JOUR
DO - 10.1002/ejoc.200901397
UR - https://doi.org/10.1002/ejoc.200901397
TI - C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction
T2 - European Journal of Organic Chemistry
AU - Trofimov, B. A.
AU - Andriyankova, Ludmila V.
AU - Belyaeva, Kseniya V
AU - Mal’kina, Anastasiya G.
AU - Nikitina, Lina P.
AU - Afonin, A.V.
AU - Ushakov, Igor
PY - 2010
DA - 2010/03/01
PB - Wiley
SP - 1772-1777
IS - 9
VL - 2010
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2010_Trofimov,
author = {B. A. Trofimov and Ludmila V. Andriyankova and Kseniya V Belyaeva and Anastasiya G. Mal’kina and Lina P. Nikitina and A.V. Afonin and Igor Ushakov},
title = {C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction},
journal = {European Journal of Organic Chemistry},
year = {2010},
volume = {2010},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/ejoc.200901397},
number = {9},
pages = {1772--1777},
doi = {10.1002/ejoc.200901397}
}
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MLA
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Trofimov, B. A., et al. “C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction.” European Journal of Organic Chemistry, vol. 2010, no. 9, Mar. 2010, pp. 1772-1777. https://doi.org/10.1002/ejoc.200901397.
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