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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
Author(s) -
Clerici Francesca,
Gelmi Maria Luisa,
Monzani Cristiano,
Pocar Donato,
Sala Alessandro
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430434
Subject(s) - isothiazole , isoxazole , cycloaddition , chemistry , yield (engineering) , nitrile , bicyclic molecule , regioselectivity , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
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.