Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes
B. A. Trofimov
1
,
Ludmila V. Andriyankova
1
,
Lina P. Nikitina
1
,
Kseniya V Belyaeva
1
,
Anastasia G Malkina
1
,
Lubov' N. Sobenina
1
,
A.V. Afonin
1
,
Igor Ushakov
1
Publication type: Journal Article
Publication date: 2013-04-25
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
23617797
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
1-Substituted imidazoles undergo exceptionally facile stereoselective ring opening under the influence of electron-deficient acetylenes and water (equimolar ratio of the reactants) in MeCN at 45-60 °C without any catalysts to afford functionalized (Z,Z)-1,4-diaza-2,5-dienes, (Z,Z)-propenylaminoethenylformamides, in up to 80% yields. The reaction is rationalized to proceed in a tandem manner via zwitterionic vinyl carbanions formed by nucleophilic addition of imidazole to the triple bond. The carbanionic center is then quenched with water followed by the rearrangement of the intermediate 2-hydroxy-3-alkenylimidazolines.
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Total citations:
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Citations from 2024:
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(11.76%)
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Trofimov B. A. et al. Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes // Organic Letters. 2013. Vol. 15. No. 9. pp. 2322-2324.
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Trofimov B. A., Andriyankova L. V., Nikitina L. P., Belyaeva K. V., Malkina A. G., Sobenina L. N., Afonin A., Ushakov I. Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes // Organic Letters. 2013. Vol. 15. No. 9. pp. 2322-2324.
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TY - JOUR
DO - 10.1021/ol400844x
UR - https://doi.org/10.1021/ol400844x
TI - Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes
T2 - Organic Letters
AU - Trofimov, B. A.
AU - Andriyankova, Ludmila V.
AU - Nikitina, Lina P.
AU - Belyaeva, Kseniya V
AU - Malkina, Anastasia G
AU - Sobenina, Lubov' N.
AU - Afonin, A.V.
AU - Ushakov, Igor
PY - 2013
DA - 2013/04/25
PB - American Chemical Society (ACS)
SP - 2322-2324
IS - 9
VL - 15
PMID - 23617797
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2013_Trofimov,
author = {B. A. Trofimov and Ludmila V. Andriyankova and Lina P. Nikitina and Kseniya V Belyaeva and Anastasia G Malkina and Lubov' N. Sobenina and A.V. Afonin and Igor Ushakov},
title = {Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes},
journal = {Organic Letters},
year = {2013},
volume = {15},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ol400844x},
number = {9},
pages = {2322--2324},
doi = {10.1021/ol400844x}
}
Cite this
MLA
Copy
Trofimov, B. A., et al. “Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes.” Organic Letters, vol. 15, no. 9, Apr. 2013, pp. 2322-2324. https://doi.org/10.1021/ol400844x.