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四氟硼酸锌介导的2-氮杂环丙烷羧酸酯向2-亚氨基噻唑烷和噻唑烷-2-亚氨基四氟硼酸盐的扩环反应及其抗菌活性评估

Zinc Tetrafluoroborate-Mediated Ring Expansion of -Aziridine-2-carboxylates to -2-Iminothiazolidines and -Thiazolidine-2-iminium Tetrafluoroborates and Evaluation of Antimicrobial Activity.

作者信息

Ben Maamer Chayma, Dridi Rihab, Lahmar Malek, Tabarki Mohamed Ali, Jobran Mariem, Sahtel Sami, Zid Mohamed Faouzi, Ouzari Hadda Imene, Vrancken Emmanuel, Besbes Rafâa

机构信息

UMR 5253 CNRS-UM-ENSCM, Institut Charles Gerhardt de Montpellier, 240 avenue du Professeur Emile Jeanbrau, 34296 Cedex 5 Montpellier, France.

Faculty of Sciences of Tunis, Department of Chemistry, Laboratory of Analytical Chemistry and Electrochemistry,University of Tunis El Manar, Campus Universities,2092 Tunis El Manar, Tunisia.

出版信息

ACS Omega. 2023 Aug 8;8(33):30402-30409. doi: 10.1021/acsomega.3c03531. eCollection 2023 Aug 22.

DOI:10.1021/acsomega.3c03531
PMID:37636906
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10448496/
Abstract

-2-iminothiazolidines and -thiazolidine-2-iminium tetrafluoroborates were successfully produced from --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 -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 -thiazolidine-2-iminium salts showed growth inhibition against .

摘要

在回流的1,2-二氯乙烷中，通过四氟硼酸锌介导，由2-烷基氮杂环丙烷-2-羧酸盐和苯基/烷基异硫氰酸酯成功制备了-2-亚氨基噻唑烷和-噻唑烷-2-亚氨基四氟硼酸盐。反应通过完全区域和立体选择性过程进行，以中等至良好的产率（35%至82%）得到标题亚氨基噻唑烷和-噻唑烷-2-亚氨基盐，底物范围广泛。此外，对这些化合物的抗菌活性评估以及最低抑菌浓度（MIC）测定表明，只有四种-噻唑烷-2-亚氨基盐对……显示出生长抑制作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/8fedd05b51aa/ao3c03531_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/fed3478cf733/ao3c03531_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/6f4a6903cc2d/ao3c03531_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/90815b6957bd/ao3c03531_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/8fedd05b51aa/ao3c03531_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/fed3478cf733/ao3c03531_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/6f4a6903cc2d/ao3c03531_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/90815b6957bd/ao3c03531_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1570/10448496/8fedd05b51aa/ao3c03531_0002.jpg

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本文引用的文献

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Enantiospecific Aluminum-Catalyzed (3+2) Cycloaddition of Unactivated Aziridines with Isothiocyanates.非手性铝催化的未活化氮丙啶与异硫氰酸酯的（3+2）环加成反应。
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Stereospecific Synthesis of 2-Iminothiazolidines via Domino Ring-Opening Cyclization of Activated Aziridines with Aryl- and Alkyl Isothiocyanates.通过活性氮杂环丙烷与芳基和烷基异硫氰酸酯的多米诺开环环化反应立体选择性合成 2-亚氨基噻唑烷。
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