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Eelectrosynthesis of benzothiazole derivatives via C–H thiolation
Heterocyclic Communications ( IF 2.3 ) Pub Date : 2022-01-01 , DOI: 10.1515/hc-2022-0008
Reza Ahdenov 1 , Ali Asghar Mohammadi 2 , Somayeh Makarem 3 , Salman Taheri 1 , Hoda Mollabagher 1
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Abstract Benzothiazole derivatives are essential intermediates in synthesizing a wide variety of medical and pharmaceutical compounds, and there is a great demand for a simple and efficient method to synthesize benzothiazoles under mild reaction conditions. Organic electrosynthesis as an energy-efficient process represents an environmentally benign and safer method than traditional methods for organic synthesis. Herein, we present bromine-free and straightforward synthesis of 2-amino benzothiazole derivatives via the reaction of aniline derivatives and ammonium thiocyanate using electrosynthesis in the presence of sodium bromide both as an electrolyte and as a brominating agent at room temperature in isopropyl alcohol (i-PrOH) as a solvent. The reaction of ammonium thiocyanate via C–H thiolation routes, using various aniline derivatives, resulted in a simple, green, and bromine-free synthesis of 2-amino benzothiazole in moderate to good yields under mild reaction conditions. Riluzole drug can be produced using the same procedure in moderate yields.

中文翻译:

C-H硫醇化电合成苯并噻唑衍生物

摘要 苯并噻唑衍生物是合成多种医药化合物必不可少的中间体,迫切需要一种简单、高效、反应条件温和的苯并噻唑类化合物合成方法。有机电合成作为一种节能工艺,与传统的有机合成方法相比,是一种环境友好且更安全的方法。在此,我们提出了通过苯胺衍生物和硫氰酸铵的反应,在溴化钠作为电解质和溴化剂的存在下,在室温下在异丙醇中进行无溴且直接的合成 2-氨基苯并噻唑衍生物(i -PrOH) 作为溶剂。硫氰酸铵通过 C-H 硫醇化路线的反应,使用各种苯胺衍生物,在温和的反应条件下以中等至良好的收率合成了简单、绿色和无溴的 2-氨基苯并噻唑。利鲁唑药物可以使用相同的程序以中等产量生产。
更新日期:2022-01-01
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