Cargando…
cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
[Image: see text] 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 no...
| Autores principales: | , , , , , , |
|---|---|
| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2021
|
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8427784/ https://www.ncbi.nlm.nih.gov/pubmed/34514245 http://dx.doi.org/10.1021/acsomega.1c03063 |
| _version_ | 1783750243021488128 |
|---|---|
| author | Filatov, Vadim E. Kuznetsova, Juliana Petrovskaya, Lada Yuzabchuk, Dmitry Tafeenko, Victor A. Zyk, Nikolay V. Beloglazkina, Elena K. |
| author_facet | Filatov, Vadim E. Kuznetsova, Juliana Petrovskaya, Lada Yuzabchuk, Dmitry Tafeenko, Victor A. Zyk, Nikolay V. Beloglazkina, Elena K. |
| author_sort | Filatov, Vadim E. |
| collection | PubMed |
| description | [Image: see text] 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-MeOC(6)H(4)CH(2)COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated. |
| format | Online Article Text |
| id | pubmed-8427784 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2021 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-84277842021-09-10 cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent Filatov, Vadim E. Kuznetsova, Juliana Petrovskaya, Lada Yuzabchuk, Dmitry Tafeenko, Victor A. Zyk, Nikolay V. Beloglazkina, Elena K. ACS Omega [Image: see text] 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-MeOC(6)H(4)CH(2)COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated. American Chemical Society 2021-08-26 /pmc/articles/PMC8427784/ /pubmed/34514245 http://dx.doi.org/10.1021/acsomega.1c03063 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
| spellingShingle | Filatov, Vadim E. Kuznetsova, Juliana Petrovskaya, Lada Yuzabchuk, Dmitry Tafeenko, Victor A. Zyk, Nikolay V. Beloglazkina, Elena K. cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent |
| title | cis-Diastereoselective Synthesis
of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with
TsCl as Activating Co-reagent |
| title_full | cis-Diastereoselective Synthesis
of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with
TsCl as Activating Co-reagent |
| title_fullStr | cis-Diastereoselective Synthesis
of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with
TsCl as Activating Co-reagent |
| title_full_unstemmed | cis-Diastereoselective Synthesis
of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with
TsCl as Activating Co-reagent |
| title_short | cis-Diastereoselective Synthesis
of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with
TsCl as Activating Co-reagent |
| title_sort | cis-diastereoselective synthesis
of spirooxindolo-β-lactams by staudinger cycloaddition with
tscl as activating co-reagent |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8427784/ https://www.ncbi.nlm.nih.gov/pubmed/34514245 http://dx.doi.org/10.1021/acsomega.1c03063 |
| work_keys_str_mv | AT filatovvadime cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT kuznetsovajuliana cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT petrovskayalada cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT yuzabchukdmitry cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT tafeenkovictora cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT zyknikolayv cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent AT beloglazkinaelenak cisdiastereoselectivesynthesisofspirooxindoloblactamsbystaudingercycloadditionwithtsclasactivatingcoreagent |