Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds
Publication type: Journal Article
Publication date: 2022-08-25
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36007261
Organic Chemistry
Abstract
A novel carbenoid-mediated approach to thioisomünchnones was developed by intermolecular copper-catalyzed reactions of diazoacetamides with aromatic and heteroaromatic thioamides bearing a pyrrolidine moiety. The direction of the reaction can be switched toward 2-amino-2-heteroarylacrylamides by replacing the pyrrolidine with an aniline group or by the use of 2-cyano-2-diazoacetamides. The proposed mechanism and DFT calculations allowed us to rationalize the effect of substituents on the reaction direction. Effective methods were found for the synthesis of previously unknown both 2-heteroarylthioisomünchones and 2-heteroarylacrylamides, based on a wide scope of available reagents with a similar structure. Some of the synthesized thioisomünchnones exhibited multicolor fluorescence in the solid state and solutions.
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Ilkin V. G. et al. Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12196-12213.
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Ilkin V. G., Filimonov V. O., Seliverstova E. A., Novikov M. S., Beryozkina T. V., Gagarin A. A., Belskaya N. P., Muthipeedika N. J., Bakulev V. A., Dehaen W. Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12196-12213.
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TY - JOUR
DO - 10.1021/acs.joc.2c01352
UR - https://doi.org/10.1021/acs.joc.2c01352
TI - Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds
T2 - Journal of Organic Chemistry
AU - Ilkin, Vladimir G
AU - Filimonov, Valeriy O
AU - Seliverstova, Eugenia A
AU - Novikov, Mikhail S.
AU - Beryozkina, Tetyana V
AU - Gagarin, Aleksey A.
AU - Belskaya, Nataliya P.
AU - Muthipeedika, Nibin Joy
AU - Bakulev, Vasiliy A.
AU - Dehaen, Wim
PY - 2022
DA - 2022/08/25
PB - American Chemical Society (ACS)
SP - 12196-12213
IS - 18
VL - 87
PMID - 36007261
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Ilkin,
author = {Vladimir G Ilkin and Valeriy O Filimonov and Eugenia A Seliverstova and Mikhail S. Novikov and Tetyana V Beryozkina and Aleksey A. Gagarin and Nataliya P. Belskaya and Nibin Joy Muthipeedika and Vasiliy A. Bakulev and Wim Dehaen},
title = {Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.2c01352},
number = {18},
pages = {12196--12213},
doi = {10.1021/acs.joc.2c01352}
}
Cite this
MLA
Copy
Ilkin, Vladimir G., et al. “Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds.” Journal of Organic Chemistry, vol. 87, no. 18, Aug. 2022, pp. 12196-12213. https://doi.org/10.1021/acs.joc.2c01352.