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article · ACS Omega

Zinc Tetrafluoroborate-Mediated Ring Expansion of <i>trans</i>-Aziridine-2-carboxylates to <i>cis</i>-2-Iminothiazolidines and <i>cis</i>-Thiazolidine-2-iminium Tetrafluoroborates and Evaluation of Antimicrobial Activity

20232 citationsOpen accessUniversity of Tunis El Manar

Abstract

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.

Research topics

  • Synthesis and Catalytic Reactions
  • Phenothiazines and Benzothiazines Synthesis and Activities
  • Sulfur-Based Synthesis Techniques

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DOI: 10.1021/acsomega.3c03531

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