Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates
Publication type: Journal Article
Publication date: 2014-08-15
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
A new method has been developed for the synthesis of benzimidazole carbothioamides, which have potential pharmacological activity, by a three-component reaction of 1-substituted benzimidazoles, phenylcyanoacetylene, and methyl, allyl, or phenyl isothiocyanates. The reaction of these components proceeds under mild conditions in acetonitrile at 50-55°C for 12-20 h and stereoselectively leads to N-[(Z)-2-cyano-1-phenylethenyl]benzimidazole-2-carbothioamides in 43-82% yield.
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Andriyankova L. V. et al. Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates // Chemistry of Heterocyclic Compounds. 2014. Vol. 50. No. 6. pp. 807-813.
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Andriyankova L. V., Nikitina L. P., Belyaeva K. V., Malkina A. G., Afonin A. V., Vashchenko A. V., Smirnov V. I., Trofimov B. A. Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates // Chemistry of Heterocyclic Compounds. 2014. Vol. 50. No. 6. pp. 807-813.
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TY - JOUR
DO - 10.1007/s10593-014-1535-y
UR - https://doi.org/10.1007/s10593-014-1535-y
TI - Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates
T2 - Chemistry of Heterocyclic Compounds
AU - Andriyankova, L V
AU - Nikitina, L. P.
AU - Belyaeva, K V
AU - Malkina, A G
AU - Afonin, A V
AU - Vashchenko, A V
AU - Smirnov, V. I.
AU - Trofimov, B. A.
PY - 2014
DA - 2014/08/15
PB - Springer Nature
SP - 807-813
IS - 6
VL - 50
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2014_Andriyankova,
author = {L V Andriyankova and L. P. Nikitina and K V Belyaeva and A G Malkina and A V Afonin and A V Vashchenko and V. I. Smirnov and B. A. Trofimov},
title = {Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates},
journal = {Chemistry of Heterocyclic Compounds},
year = {2014},
volume = {50},
publisher = {Springer Nature},
month = {aug},
url = {https://doi.org/10.1007/s10593-014-1535-y},
number = {6},
pages = {807--813},
doi = {10.1007/s10593-014-1535-y}
}
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MLA
Copy
Andriyankova, L. V., et al. “Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates.” Chemistry of Heterocyclic Compounds, vol. 50, no. 6, Aug. 2014, pp. 807-813. https://doi.org/10.1007/s10593-014-1535-y.