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Novel Synthesis of 2-Aryl-4,5,6,7-tetrahydro-1,2-benzisothiazol-3(2H)-ones and Their S-Oxides

✍ Scribed by Anja Siegemund; Christine Hartung; Sven Baumann; Bärbel Schulze

Publisher: John Wiley and Sons
Year: 2004
Tongue: German
Weight: 110 KB
Volume: 87
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200490035

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✦ Synopsis

Abstract

2‐Aryl‐4,5,6,7‐tetrahydro‐1,2‐benzisothiazol‐3(2__H__)‐ones 1a–e were synthesized by cyclocondensation of 2‐(thiocyanato)cyclohexene‐1‐carboxanilides 9 as a convenient new method. Their S‐oxides 10 were prepared by two routes, either by oxidation of 1 or dehydration of rac‐cis‐3‐hydroperoxysultims 11. Furthermore, compounds 1 have been identified by HPLCAPI‐MS‐MS as intermediates in the oxidation process of the salts 6. The hydroperoxides 12b and rac‐trans‐11b have been unambiguously detected by HPLCMS investigations and in the reaction of rac‐cis‐13b with H~2~O~2~ to the hydroperoxides rac‐trans‐11b and rac‐cis‐11b.

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