N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives
Publication type: Journal Article
Publication date: 2020-07-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
4-Oxo-1,4-dihydrocinnoline derivatives as promising inhibitors of protein tyrosine phosphatase 1В were subjected to post-synthetic modification via a sequence of propargylation and copper(I)-catalyzed azide-alkyne cycloaddition reactions. The propargylation of 4-oxo- 1,4-dihydrocinnolines with propargyl bromide in the presence of various bases proceeded regioselectively at the cinnolinone N-1 atom. In the cycloaddition reaction of N-propargylcinnolinones and benzyl azide, the highest catalytic activity of copper(I) N-heterocyclic carbene complex [(IMes)Cu(Br,I)] was observed, compared to [(IMes)CuCl], [(IPr)Cu(Cl,Br,I)], and CuI.
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Total citations:
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Citations from 2024:
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(38.46%)
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Mikhaylov V. N. et al. N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 915-922.
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Mikhaylov V. N., Pavlov A. O., Ogorodnov Y. V., Spiridonova D. V., Sorokoumov V. N., Balova I. A. N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 915-922.
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TY - JOUR
DO - 10.1007/s10593-020-02750-0
UR - https://doi.org/10.1007/s10593-020-02750-0
TI - N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives
T2 - Chemistry of Heterocyclic Compounds
AU - Mikhaylov, Vladimir N.
AU - Pavlov, Artem O
AU - Ogorodnov, Yaroslav V
AU - Spiridonova, Darya V
AU - Sorokoumov, Viktor N
AU - Balova, Irina A
PY - 2020
DA - 2020/07/01
PB - Springer Nature
SP - 915-922
IS - 7
VL - 56
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2020_Mikhaylov,
author = {Vladimir N. Mikhaylov and Artem O Pavlov and Yaroslav V Ogorodnov and Darya V Spiridonova and Viktor N Sorokoumov and Irina A Balova},
title = {N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives},
journal = {Chemistry of Heterocyclic Compounds},
year = {2020},
volume = {56},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007/s10593-020-02750-0},
number = {7},
pages = {915--922},
doi = {10.1007/s10593-020-02750-0}
}
Cite this
MLA
Copy
Mikhaylov, Vladimir N., et al. “N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives.” Chemistry of Heterocyclic Compounds, vol. 56, no. 7, Jul. 2020, pp. 915-922. https://doi.org/10.1007/s10593-020-02750-0.