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Zur Oxidation von 1,2‐Thiazolen: Ein einfacher Zugang zu 1,2‐Thiazol‐3(2 H )‐on‐1,1‐dioxiden
Author(s) -
Schulze Bärbel,
Kirsten Gisela,
Kirrbach Sabine,
Rahm Annette,
Heimgartner Heinz
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740515
Subject(s) - chemistry , medicinal chemistry , ammonia , ammonium thiocyanate , oxaziridine , dimethyldioxirane , stereochemistry , organic chemistry
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.