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Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxiden

✍ Scribed by Bärbel Schulze; Gisela Kirsten; Sabine Kirrbach; Annette Rahm; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
734 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Oxidation of 1,2‐Thiazoles; A Convenient Approach to 1,2‐Thiazol‐3(2__H__)‐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(2__H__)‐one 1,1‐dioxidcs 10 on treatment with H~2~O~2~ in AcOH at 80°. Hydrogenation of 10 in AcOH yields the corresponding saturated 1,2‐thiazolidin‐3‐one 1,1‐dioxides 16 (Scheme 3). Cycloalka[c]‐1,2‐thiazoles 18 are prepared from 2‐[(thiocyanato)methyliden]cycloalkan‐1‐ones and ammonia (Scheme 4). Surprisingly, oxidation of 18a with H~2~O~2~ in AcOH yields the tricyclic oxaziridine 19.

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