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吩噻嗪的可持续电化学膦酰化反应。具有强大抗菌活性的C-鏻甜菜碱的合成。

A sustainable electrochemical phosphonylation of phenothiazine. Synthesis of a C-phosphonium betaine with powerful antibacterial activity.

作者信息

Gitipeimay Hamedani Mahtab, Nematollahi Davood, Goudarztalejerdi Ali, Mohamadighader Niloofar, Lotfipour Farideh

机构信息

Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University Hamedan 65178-38683 Iran

Planet Chemistry Research Center, Bu-Ali Sina University Hamedan Iran.

出版信息

RSC Adv. 2025 Jul 31;15(33):27246-27253. doi: 10.1039/d5ra03690a. eCollection 2025 Jul 25.

DOI:10.1039/d5ra03690a
PMID:40746782
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12311779/
Abstract

To demonstrate the capabilities of electrochemistry in the synthesis of organic compounds, we developed a facile and sustainable direct electrochemical phosphonylation of phenothiazine with triphenylphosphine. In this work, we demonstrated that electrochemically produced phenothiazine-5-ium can react with triphenylphosphine in a water/acetonitrile mixture under simple conditions using graphite and stainless steel electrodes in an undivided cell, galvanostatically and without the use of any catalyst, to synthesize the corresponding C-phosphonium betaine in good yield. The synthesized phosphonium betaine shows strong antibacterial activity against a variety of Gram positive and negative bacteria.

摘要

为了展示电化学在有机化合物合成中的能力,我们开发了一种简便且可持续的方法,即吩噻嗪与三苯基膦的直接电化学膦酰化反应。在这项工作中,我们证明了电化学产生的吩噻嗪 -5- 鎓能在水 / 乙腈混合溶剂中,于简单条件下,使用石墨和不锈钢电极在无隔膜电解池中,恒电流且不使用任何催化剂的情况下,与三苯基膦反应,以良好的产率合成相应的 C- 磷鎓甜菜碱。合成的磷鎓甜菜碱对多种革兰氏阳性和阴性细菌表现出强大的抗菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3399/12311779/346bbf909edc/d5ra03690a-f6.jpg
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