Isothiazoles. Part V. 1cycloaddition reaction of nitrite oxides to 3 diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide: an entry to 5-acyl- and 5-cyano-isothiazole 1,1-dioxide derivatives
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Add time:07/19/2019 Source:sciencedirect.com
Nitrile oxides 2 reacted with 3-diethylamino 4(4 methoxyphenyl)-isothiazole 1,1 dioxide (1) affording through a highly regioselective 1,3-dipolar cycloaddition reaction isothiazolo[5,4-d]isoxazoline 4,4 dioxides 3. Reduction of 3 afforded a mixture of the E and Z forms of the corresponding 5-(amino-aryl methylene]-dihydro-isothiazole 1,1-dioxides 4/5 which were transformed into 5-acyl-dihydro-isothiazole 1,1dioxides 6 and the corresponding dehydrated products 7. Compound 3f was easily transformed into 5-cyanoisothiazole 1,1-dioxide 11
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