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Synthesis of Monocyclic Hydroperoxy‐ and Hydroxy‐Substituted Sulfin‐ and Sulfonamides by Oxidation of 4,5‐Dimethylisothiazolium Salts
Author(s) -
Taubert Kathleen,
Sieler Joachim,
Hennig Lothar,
Findeisen Matthias,
Schulze Bärbel
Publication year - 2002
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 - 10.1002/1522-2675(200201)85:1<183::aid-hlca183>3.0.co;2-5
Subject(s) - chemistry , salt (chemistry) , aryl , medicinal chemistry , organic chemistry , alkyl
The isothiazolium salts 10 , easily accessible by cyclocondensation of the thiocyanates 8 with the anilines 9 , yielded with H 2 O 2 as the oxidant the first stable hydroperoxides of the 2‐aryl‐2,3‐dihydroisothiazole 1‐oxides rac‐cis ‐ 13 , the 1,1‐dioxides 15 , and their reduced 3‐hydroxy derivatives rac‐cis ‐ 14 and 16 , respectively. The oxidation of 10 to new isothiazol‐3(2 H )‐one 1,1‐dioxides ( 17 ) is also described. For the first time, an aryl‐bridged bis[isothiazolium salt] 11 was synthesized and oxidized.