Synthesis of Monocyclic Hydroperoxy- and Hydroxy-Substituted Sulfin- and Sulfonamides by Oxidation of 4,5-Dimethylisothiazolium Salts

Abstract

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(2H)-one 1,1-dioxides (17) is also described. For the first time, an arylbridged bis[isothiazolium salt] 11 was synthesized and oxidized.

2,4,5-Triphenylisothiazol-3(2H)-one 1,1-dioxides as inhibitors of human leukocyte elastase

“…The synthetic route to isothiazol-3(2H)-one dioxides 9 is shown in Scheme 1, and detailed information on these reactions are given elsewhere [27,30,31]. Isothiazolium salts 7 were obtained from the reaction of thiocyanates 5 with the substituted anilines 6.…”