Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxiden |
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| Authors: | Brbel Schulze Gisela Kirsten Sabine Kirrbach Annette Rahm Heinz Heimgartner |
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| Institution: | Bärbel Schulze,Gisela Kirsten,Sabine Kirrbach,Annette Rahm,Heinz Heimgartner |
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| Abstract: | Oxidation of 1,2-Thiazoles; A Convenient Approach to 1,2-Thiazol-3(2H)-one 1,1-Dioxides The 1,2-thiazoles obtained from 3-chloroalk-2-enals and ammonium thiocyanate ( 7 → 9 , Scheme 1) are easily transformed to 1,2-thiazol-3(2H)-one 1,1-dioxidcs 10 on treatment with H2O2 in AcOH at 80°. Hydrogenation of 10 in AcOH yields the corresponding saturated 1,2-thiazolidin-3-one 1,1-dioxides 16 (Scheme 3). Cycloalkac]-1,2-thiazoles 18 are prepared from 2-(thiocyanato)methyliden]cycloalkan-1-ones and ammonia (Scheme 4). Surprisingly, oxidation of 18a with H2O2 in AcOH yields the tricyclic oxaziridine 19. |
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