O. Carugo et al., ISOTHIAZOLES .2. REACTION OF LAMINO-4-(4-METHOXYPHENYL)-ISOTHIAZOLE-1,1-DIOXIDE WITH SODIUM-AZIDE, Tetrahedron, 49(40), 1993, pp. 9117-9126
lamino-4-(4-methoxyphenyl)-isothiazole-1,1-dioxide 1, was reacted with
the azide ion in different solvents. Depending on reaction conditions
-1H-isothiazole-[4,5-d]-1,2,3-triazole-6,6-dioxide 3 and/or hydro-3a-
(4-methoxyphenyl)-1H-isothiazole-[4,5-d]- 1,2,3- triazole-6,6-dioxide
4 were formed. When ethanol or acetone were used as reaction solvent t
he formation of the above compounds was accompanied by solvent additio
n forming (4-methoxyphenyl)-5-ethoxy-isothiazole-1,1-dioxide 2 and oxy
phenyl)-5-(2-oxopropyl)-isothiazole-1,1-dioxide 6, respectively. React
ion mechanisms and structures of products are discussed.