Open Access
ACS Omega, volume 6, issue 35, pages 22740-22751
Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
Filatov Vadim
1
,
Kuznetsova Juliana
1
,
Petrovskaya Lada
1
,
Yuzabchuk Dmitry
1
,
Тафеенко В. А.
1
,
Zyk Nikolay V.
1
,
Publication type: Journal Article
Publication date: 2021-08-26
PubMed ID:
34514245
General Chemistry
General Chemical Engineering
Abstract
A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-β-lactams from isatin Schiff bases and substituted phenylacetic acids using ketene–imine cycloaddition reaction with TsCl for a ketene generation has been developed. The reaction procedure does not require absolute solvents and unstable starting reagents. The studied reactions lead to cis-diastereoselective β-lactam formation for all tested phenylacetic acids except 4-MeOC6H4CH2COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.
Citations by journals
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1
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International Journal of Molecular Sciences
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International Journal of Molecular Sciences
1 publication, 20%
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Mendeleev Communications
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Mendeleev Communications
1 publication, 20%
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Polyhedron
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Polyhedron
1 publication, 20%
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Progress in Heterocyclic Chemistry
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Progress in Heterocyclic Chemistry
1 publication, 20%
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Organic and Biomolecular Chemistry
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Organic and Biomolecular Chemistry
1 publication, 20%
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1
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Citations by publishers
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1
2
3
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Elsevier
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Elsevier
3 publications, 60%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 20%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 20%
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1
2
3
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Filatov V. et al. Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent // ACS Omega. 2021. Vol. 6. No. 35. pp. 22740-22751.
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Filatov V., Kuznetsova J., Petrovskaya L., Yuzabchuk D., Тафеенко В. А., Zyk N. V., Beloglazkina E. K. Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent // ACS Omega. 2021. Vol. 6. No. 35. pp. 22740-22751.
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TY - JOUR
DO - 10.1021/acsomega.1c03063
UR - https://doi.org/10.1021%2Facsomega.1c03063
TI - Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
T2 - ACS Omega
AU - Kuznetsova, Juliana
AU - Petrovskaya, Lada
AU - Yuzabchuk, Dmitry
AU - Zyk, Nikolay V.
AU - Beloglazkina, Elena K.
AU - Filatov, Vadim
AU - Тафеенко, В. А.
PY - 2021
DA - 2021/08/26 00:00:00
PB - American Chemical Society (ACS)
SP - 22740-22751
IS - 35
VL - 6
PMID - 34514245
SN - 2470-1343
ER -
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@article{2021_Filatov,
author = {Juliana Kuznetsova and Lada Petrovskaya and Dmitry Yuzabchuk and Nikolay V. Zyk and Elena K. Beloglazkina and Vadim Filatov and В. А. Тафеенко},
title = {Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent},
journal = {ACS Omega},
year = {2021},
volume = {6},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Facsomega.1c03063},
number = {35},
pages = {22740--22751},
doi = {10.1021/acsomega.1c03063}
}
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MLA
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Filatov, Vadim, et al. “Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent.” ACS Omega, vol. 6, no. 35, Aug. 2021, pp. 22740-22751. https://doi.org/10.1021%2Facsomega.1c03063.
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