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Isothiazolo[5,4-d]isoxazole S,S-dioxides and pyrazolo [3,4-d]-isothiazole S,S-dioxides through cycloaddition reaction on 3-benzylaminoisothiazole S,S-dioxides

✍ Scribed by Francesca Clerici; Maria Luisa Gelmi; Cristiano Monzani; Donato Pocar; Alessandro Sala

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 86 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430434

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✦ Synopsis

Abstract

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By reacting 4,5‐unsubstituted isothiazole dioxides with diazoalkanes and nitrile oxides bicyclic pyrazolo[3,4‐d]isothiazole and isothiazolo[5,4‐d]isoxazole S,S‐dioxides were obtained in good yield through a regioselective cycloaddition reaction. Through cycloaddition reaction of 3‐benzylamino‐4‐bromo‐isothiazole S,S‐dioxide labile cycloadducts were formed that underwent in situ dehydrobromination affording the corresponding aromatized compounds.

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