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ACS Omega

, том 6 , издание 35 , страницы 22740-22751

Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent

Тип публикации: Journal Article

Дата публикации: 2021-08-26

American Chemical Society (ACS)

ACS Omega

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SJR: 0.773

CiteScore: 7.1

Impact factor: 4.3

ISSN: 24701343

DOI: 10.1021/acsomega.1c03063

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PubMed ID: 34514245

General Chemistry

General Chemical Engineering

Краткое описание

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.

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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., Filatov V. E., Kuznetsova J., Petrovskaya L., Yuzabchuk D., Тафеенко В. А., Tafeenko V. A., 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://pubs.acs.org/doi/10.1021/acsomega.1c03063

TI - Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent

T2 - ACS Omega

AU - Filatov, Vadim

AU - Filatov, Vadim E

AU - Kuznetsova, Juliana

AU - Petrovskaya, Lada

AU - Yuzabchuk, Dmitry

AU - Тафеенко, В. А.

AU - Tafeenko, Victor A.

AU - Zyk, Nikolay V.

AU - Beloglazkina, Elena K.

PY - 2021

DA - 2021/08/26

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 = {Vadim Filatov and Vadim E Filatov and Juliana Kuznetsova and Lada Petrovskaya and Dmitry Yuzabchuk and В. А. Тафеенко and Victor A. Tafeenko and Nikolay V. Zyk and Elena K. Beloglazkina},

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://pubs.acs.org/doi/10.1021/acsomega.1c03063},

number = {35},

pages = {22740--22751},

doi = {10.1021/acsomega.1c03063}

}

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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://pubs.acs.org/doi/10.1021/acsomega.1c03063.