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

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 p...

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Published in:ACS omega 2023-08, Vol.8 (33), p.30402-30409
Main Authors: Ben Maamer, Chayma, Dridi, Rihab, Lahmar, Malek, Tabarki, Mohamed Ali, Jobran, Mariem, Sahtel, Sami, Zid, Mohamed Faouzi, Ouzari, Hadda Imene, Vrancken, Emmanuel, Besbes, Rafâa
Format: Article
Language:English
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Chemical Sciences
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Summary: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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.3c03531