Stereoselective synthesis of (E)-4-alkoxy-2-aryl-5-chloro-2-thiazolines |
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Authors: | Antonio Guirado Raquel Andreu Bruno Martiz Sergio Pérez-Ballester |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, 30071 Murcia, Apartado 4021, Spain |
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Abstract: | The first synthesis of the title compounds has been achieved starting from chloralamides by a route involving chemical and electrochemical steps. N-(1-Alkoxy-2,2,2-trichloroethyl)benzamides were efficiently prepared from chloralbenzamides and were electrochemically converted into N-(1-alkoxy-2,2-dichloroethyl)benzamides in high yields by cathodic reduction in a protic medium. Thionation of these compounds with Lawesson's reagent followed by basic treatment gave novel (E)-4-alkoxy-2-aryl-5-chloro-2-thiazolines in fair to quantitative yields. |
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Keywords: | Thiazolines Chloralamides Reduction Thionation Electrosynthesis |
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