Georg Thieme Verlag KG
Synlett
,  volume 23 ,  issue 14 ,  pages 2069-2072

Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides

B. A. Trofimov 1
, 
Ludmila Andriyankova 1
, 
Lina Nikitina 1
, 
Kseniya Belyaeva 1
, 
Anastasiya Malkina 1
, 
A.V. Afonin 1
, 
Igor Ushakov 1
1
 
Publication type: Journal Article
Publication date: 2012-08-08
Georg Thieme Verlag KG
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Abstract
N-(Z)-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst- and solvent-free conditions at room temperature. The reaction proceeds via zwitterion–carbene intermediates which are trapped by isothiocyanates to form the zwitterion with ambident N–S anionic site, which then undergoes stereo- and regioselective migration of the alkenyl moiety.
Found 
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GOST Copy
Trofimov B. A. et al. Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides // Synlett. 2012. Vol. 23. No. 14. pp. 2069-2072.
GOST all authors (up to 50) Copy
Trofimov B. A., Andriyankova L., Nikitina L., Belyaeva K., Malkina A., Afonin A., Ushakov I. Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides // Synlett. 2012. Vol. 23. No. 14. pp. 2069-2072.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0031-1290442
UR - https://doi.org/10.1055/s-0031-1290442
TI - Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides
T2 - Synlett
AU - Trofimov, B. A.
AU - Andriyankova, Ludmila
AU - Nikitina, Lina
AU - Belyaeva, Kseniya
AU - Malkina, Anastasiya
AU - Afonin, A.V.
AU - Ushakov, Igor
PY - 2012
DA - 2012/08/08
PB - Georg Thieme Verlag KG
SP - 2069-2072
IS - 14
VL - 23
SN - 0936-5214
SN - 1437-2096
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Trofimov,
author = {B. A. Trofimov and Ludmila Andriyankova and Lina Nikitina and Kseniya Belyaeva and Anastasiya Malkina and A.V. Afonin and Igor Ushakov},
title = {Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides},
journal = {Synlett},
year = {2012},
volume = {23},
publisher = {Georg Thieme Verlag KG},
month = {aug},
url = {https://doi.org/10.1055/s-0031-1290442},
number = {14},
pages = {2069--2072},
doi = {10.1055/s-0031-1290442}
}
MLA
Cite this
MLA Copy
Trofimov, B. A., et al. “Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides.” Synlett, vol. 23, no. 14, Aug. 2012, pp. 2069-2072. https://doi.org/10.1055/s-0031-1290442.
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