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Conversion of bis(o-nitrophenyl)disulfides to heterocycles containing sulfur and nitrogen by the action of samarium diiodide

✍ Scribed by Weihui Zhong; Xiaoyuan Chen; Yongmin Zhang

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
78 KB
Volume
12
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Treatment of bis(o‐nitrophenyl)disulfides 1 with SmI~2~ led to simultaneous reduction of nitro groups and reductive cleavage of S–S bonds as well as the formation of the active intermediates 2. The intermediates 2 reacted smoothly with aldehydes or ketones, acid chlorides or anhydrides, α‐bromoketones, and α,β‐unsaturated ketones at room temperature to afford the desired benzothiazolines 3, benzothiazoles 4, 2H‐1,4‐benzothiazines 5, and 2,3‐dihydro‐1,5‐benzothiazepines 6, respectively, in moderate to high yields under mild and neutral conditions. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:156–160, 2001

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