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Synthesis of oxidized 1,2,3-thiadiazines by hydroperoxy-induced ring enlargement of 2-benzenesulfonylaminoisothiazolium salts

✍ Scribed by Arne Kolberg; Joachim Sieler; Bärbel Schulze

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
356 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Oxidation of 2‐benzenesulfonylaminoisothiazolium salts 1, 2 and their imines 3, 4 with hydrogen peroxide gave 1,2,3‐thiadiazine 1‐oxides 5, 6, which were converted into the corresponding 1,2,3‐thiadiazine 1,1‐dioxides 7, 8 using m‐chloroperoxybenzoic acid. Oxidation of 5, 6 with hydrogen peroxide furnished isothiazol‐3(2__H__)‐one 1,1‐dioxides 9, 10 as ring contraction products.

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