C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction
B. A. Trofimov
1
,
Ludmila V. Andriyankova
1
,
Kseniya V Belyaeva
1
,
Anastasiya G. Mal’kina
1
,
Lina P. Nikitina
1
,
A.V. Afonin
1
,
Igor Ushakov
1
Publication type: Journal Article
Publication date: 2010-03-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
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.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
|
|
|
Tetrahedron Letters
5 publications, 14.71%
|
|
|
Chemistry of Heterocyclic Compounds
4 publications, 11.76%
|
|
|
Tetrahedron
3 publications, 8.82%
|
|
|
Computational and Theoretical Chemistry
2 publications, 5.88%
|
|
|
Journal of the Iranian Chemical Society
1 publication, 2.94%
|
|
|
Carbohydrate Research
1 publication, 2.94%
|
|
|
Chinese Journal of Catalysis
1 publication, 2.94%
|
|
|
Mendeleev Communications
1 publication, 2.94%
|
|
|
Journal of Molecular Structure
1 publication, 2.94%
|
|
|
Journal of Organic Chemistry
1 publication, 2.94%
|
|
|
ACS Combinatorial Science
1 publication, 2.94%
|
|
|
Organic Letters
1 publication, 2.94%
|
|
|
RSC Advances
1 publication, 2.94%
|
|
|
Journal of Carbohydrate Chemistry
1 publication, 2.94%
|
|
|
European Journal of Chemistry
1 publication, 2.94%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 2.94%
|
|
|
Organic Chemistry International
1 publication, 2.94%
|
|
|
Journal of Chemistry
1 publication, 2.94%
|
|
|
Oriental Journal Of Chemistry
1 publication, 2.94%
|
|
|
Organic Reaction Mechanisms
1 publication, 2.94%
|
|
|
Synlett
1 publication, 2.94%
|
|
|
Russian Journal of Organic Chemistry
1 publication, 2.94%
|
|
|
Russian Chemical Reviews
1 publication, 2.94%
|
|
|
1
2
3
4
5
|
Publishers
|
2
4
6
8
10
12
14
|
|
|
Elsevier
14 publications, 41.18%
|
|
|
Springer Nature
5 publications, 14.71%
|
|
|
American Chemical Society (ACS)
3 publications, 8.82%
|
|
|
Wiley
2 publications, 5.88%
|
|
|
Hindawi Limited
2 publications, 5.88%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 2.94%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 2.94%
|
|
|
Taylor & Francis
1 publication, 2.94%
|
|
|
European Journal of Chemistry
1 publication, 2.94%
|
|
|
Oriental Scientific Publishing Company
1 publication, 2.94%
|
|
|
Georg Thieme Verlag KG
1 publication, 2.94%
|
|
|
Pleiades Publishing
1 publication, 2.94%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 2.94%
|
|
|
2
4
6
8
10
12
14
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
34
Total citations:
34
Citations from 2024:
2
(5.88%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 -
Cite this
BibTex (up to 50 authors)
Copy
@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}
}
Cite this
MLA
Copy
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.