The chemistry of 2,1-benzisothiazoles. IX. The reaction of 3-chloro-substituted 2,1-benzisothiazoles with nucleophiles and the preparation of(2,1-Benzisothiazol-3-yl)acetic acid

Abstract

3-Chloro-2,1-benzisothiazole (2; R = H, R? = Cl) and 3,5-dichloro-2,1- benzisothiazole (2;R,R? = Cl) react readily with nucleophiles, and yield 3-substituted products. Acid hydrolysis of one such product, ethyl (2,1-benzisothiazol-3-yl)cyanoacetate (2; R = H, R? = CH(CN)CO₂Et),affords (2,1-benzisothiazol-3-yl)acetic acid (2; R = H, R? = CH₂CO₂H), an auxin analogue.