The Rearrangment of 3‐Aminobenzo‐[b]thiophenes to Tricyclic Benzoisothiazoles as Result of a Simple Azo‐coupling Procedure |
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| Authors: | Susann Klimas Rainer Beckert Horst Hartmann Helmar Görls |
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| Institution: | 1. Institut für Organische und Makromolekulare Chemie, Friedrich‐Schiller‐Universit?t Jena, Jena, Germany;2. Fachbereich Chemie und Lebensmittelchemie, Technische Universit?t Dresden, Dresden, Germany;3. Institut für Anorganische und Analytische Chemie, Friedrich‐Schiller‐Universit?t Jena, Jena, Germany |
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| Abstract: | As a result of the reaction of ethyl 3‐amino‐4‐dimethylamino‐benzothiophene‐2‐carboxylate ( 1 ) with 2‐thiazolediazonium salt 2 , tricyclic ethyl 5‐(thiazol‐2‐yl)‐8‐(thiazol‐2‐yldiazenyl)‐5H‐isothiazolo3,4,5‐d,e]cinnoline‐3‐carboxylate 4 , instead of the expected 7‐thiazolylazo derivative 3 , is formed. A mechanism in which sulfanyl cations occur as intermediates is proposed. |
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