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Zinc Tetrafluoroborate-Mediated Ring Expansion of trans-Aziridine-2-carboxylates to cis-2-Iminothiazolidines and cis-Thiazolidine-2-iminium Tetrafluoroborates and Evaluation of Antimicrobial Activity
[Image: see text] Cis-2-iminothiazolidines and cis-thiazolidine-2-iminium tetrafluoroborates were successfully produced from trans-N-alkyl aziridine-2-carboxylates and phenyl/alkyl isothiocyanates mediated by zinc tetrafluoroborate in refluxing DCE. Reactions were performed via a complete regio- and...
| Autores principales: | , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2023
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10448496/ https://www.ncbi.nlm.nih.gov/pubmed/37636906 http://dx.doi.org/10.1021/acsomega.3c03531 |
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| author | Ben Maamer, Chayma Dridi, Rihab Lahmar, Malek Tabarki, Mohamed Ali Jobran, Mariem Sahtel, Sami Zid, Mohamed Faouzi Ouzari, Hadda Imene Vrancken, Emmanuel Besbes, Rafâa |
| author_facet | Ben Maamer, Chayma Dridi, Rihab Lahmar, Malek Tabarki, Mohamed Ali Jobran, Mariem Sahtel, Sami Zid, Mohamed Faouzi Ouzari, Hadda Imene Vrancken, Emmanuel Besbes, Rafâa |
| author_sort | Ben Maamer, Chayma |
| collection | PubMed |
| description | [Image: see text] Cis-2-iminothiazolidines and cis-thiazolidine-2-iminium tetrafluoroborates were successfully produced from trans-N-alkyl aziridine-2-carboxylates and phenyl/alkyl isothiocyanates mediated by zinc tetrafluoroborate in refluxing DCE. Reactions were performed via a complete regio- and stereoselective process to give the title iminothiazolidines and cis-thiazolidine-2-iminium salts in moderate to good yields (35 to 82%) with a wide substrate scope. In addition, the antibacterial activity evaluation of these compounds, as well as the minimum inhibitory concentration (MIC) determination, revealed that only four cis-thiazolidine-2-iminium salts showed growth inhibition against Bacillus cereus. |
| format | Online Article Text |
| id | pubmed-10448496 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-104484962023-08-25 Zinc Tetrafluoroborate-Mediated Ring Expansion of trans-Aziridine-2-carboxylates to cis-2-Iminothiazolidines and cis-Thiazolidine-2-iminium Tetrafluoroborates and Evaluation of Antimicrobial Activity Ben Maamer, Chayma Dridi, Rihab Lahmar, Malek Tabarki, Mohamed Ali Jobran, Mariem Sahtel, Sami Zid, Mohamed Faouzi Ouzari, Hadda Imene Vrancken, Emmanuel Besbes, Rafâa ACS Omega [Image: see text] Cis-2-iminothiazolidines and cis-thiazolidine-2-iminium tetrafluoroborates were successfully produced from trans-N-alkyl aziridine-2-carboxylates and phenyl/alkyl isothiocyanates mediated by zinc tetrafluoroborate in refluxing DCE. Reactions were performed via a complete regio- and stereoselective process to give the title iminothiazolidines and cis-thiazolidine-2-iminium salts in moderate to good yields (35 to 82%) with a wide substrate scope. In addition, the antibacterial activity evaluation of these compounds, as well as the minimum inhibitory concentration (MIC) determination, revealed that only four cis-thiazolidine-2-iminium salts showed growth inhibition against Bacillus cereus. American Chemical Society 2023-08-08 /pmc/articles/PMC10448496/ /pubmed/37636906 http://dx.doi.org/10.1021/acsomega.3c03531 Text en © 2023 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 | Ben Maamer, Chayma Dridi, Rihab Lahmar, Malek Tabarki, Mohamed Ali Jobran, Mariem Sahtel, Sami Zid, Mohamed Faouzi Ouzari, Hadda Imene Vrancken, Emmanuel Besbes, Rafâa Zinc Tetrafluoroborate-Mediated Ring Expansion of trans-Aziridine-2-carboxylates to cis-2-Iminothiazolidines and cis-Thiazolidine-2-iminium Tetrafluoroborates and Evaluation of Antimicrobial Activity |
| title | Zinc Tetrafluoroborate-Mediated
Ring Expansion of trans-Aziridine-2-carboxylates
to cis-2-Iminothiazolidines
and cis-Thiazolidine-2-iminium Tetrafluoroborates
and Evaluation of Antimicrobial Activity |
| title_full | Zinc Tetrafluoroborate-Mediated
Ring Expansion of trans-Aziridine-2-carboxylates
to cis-2-Iminothiazolidines
and cis-Thiazolidine-2-iminium Tetrafluoroborates
and Evaluation of Antimicrobial Activity |
| title_fullStr | Zinc Tetrafluoroborate-Mediated
Ring Expansion of trans-Aziridine-2-carboxylates
to cis-2-Iminothiazolidines
and cis-Thiazolidine-2-iminium Tetrafluoroborates
and Evaluation of Antimicrobial Activity |
| title_full_unstemmed | Zinc Tetrafluoroborate-Mediated
Ring Expansion of trans-Aziridine-2-carboxylates
to cis-2-Iminothiazolidines
and cis-Thiazolidine-2-iminium Tetrafluoroborates
and Evaluation of Antimicrobial Activity |
| title_short | Zinc Tetrafluoroborate-Mediated
Ring Expansion of trans-Aziridine-2-carboxylates
to cis-2-Iminothiazolidines
and cis-Thiazolidine-2-iminium Tetrafluoroborates
and Evaluation of Antimicrobial Activity |
| title_sort | zinc tetrafluoroborate-mediated
ring expansion of trans-aziridine-2-carboxylates
to cis-2-iminothiazolidines
and cis-thiazolidine-2-iminium tetrafluoroborates
and evaluation of antimicrobial activity |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10448496/ https://www.ncbi.nlm.nih.gov/pubmed/37636906 http://dx.doi.org/10.1021/acsomega.3c03531 |
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