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Fused Isothiazole S-Oxide Systems from Cycloaddition Reactions of N-Benzylisothiazol-3-amine 1-Oxide

✍ Scribed by Francesca Clerici; Alessandro Casoni; Alessandro Contini; Maria L. Gelmi; Sara Pellegrino

Publisher: John Wiley and Sons
Year: 2009
Tongue: German
Weight: 266 KB
Volume: 92
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200800342

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✦ Synopsis

Abstract

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The racemic N‐benzylisothiazol‐3‐amine 1‐oxide (2) was demonstrated to be an efficient partner in Diels–Alder reactions (Schemes 2–4) and a good dipolarophile in 1,3‐dipolar cycloaddition reactions with nitrile oxides (Scheme 5). Polycyclic isothiazole S‐oxides with different substitution patterns were obtained from 2 in good yield and in a fully regioselective way. Improved diastereoselection was observed performing the Diels–Alder or 1,3‐dipolar cycloaddition reactions in H~2~O.

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