An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling
Publication type: Journal Article
Publication date: 2013-10-09
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Ullmann-type C–N coupling of vinyliodides and nitrogen heterocycles has been shown to be a straightforward and highly efficient approach to azolyl-substituted steroids. The amination reaction proved sensitive to steric effects exerted by the substituents in both iodide and heterocycle. The influence of reaction conditions (catalyst, base, solvent, and temperature) on conversion of the iodosteroid and the selectivity was investigated. The catalytic system comprising 10 mol-% CuI and 20 mol-% dipivaloylmethane with K2CO3 in dimethyl sulfoxide at 100 °C delivered the best result. The elaborated protocol has permitted iodosteroids with various substituted indoles, imidazoles, carbazole, indazole, and sec-amides to be coupled, affording the corresponding azolyl-substituted steroids in good to excellent yields.
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Total citations:
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Citations from 2024:
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(5.88%)
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Kotovshchikov Y. N. et al. An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling // European Journal of Organic Chemistry. 2013. Vol. 2013. No. 34. pp. 7823-7832.
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Kotovshchikov Y. N., Latyshev G. V., Lukashev N. V., Beletskaya I. P. An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling // European Journal of Organic Chemistry. 2013. Vol. 2013. No. 34. pp. 7823-7832.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201300719
UR - https://doi.org/10.1002/ejoc.201300719
TI - An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling
T2 - European Journal of Organic Chemistry
AU - Kotovshchikov, Yury N
AU - Latyshev, Gennadij V
AU - Lukashev, Nikolay V
AU - Beletskaya, Irina P.
PY - 2013
DA - 2013/10/09
PB - Wiley
SP - 7823-7832
IS - 34
VL - 2013
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2013_Kotovshchikov,
author = {Yury N Kotovshchikov and Gennadij V Latyshev and Nikolay V Lukashev and Irina P. Beletskaya},
title = {An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling},
journal = {European Journal of Organic Chemistry},
year = {2013},
volume = {2013},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/ejoc.201300719},
number = {34},
pages = {7823--7832},
doi = {10.1002/ejoc.201300719}
}
Cite this
MLA
Copy
Kotovshchikov, Yury N., et al. “An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling.” European Journal of Organic Chemistry, vol. 2013, no. 34, Oct. 2013, pp. 7823-7832. https://doi.org/10.1002/ejoc.201300719.