Abstract
In continuation of our studies on the acetylation and alkylation reactions of 3,4-dihydro-2H-1,2,3-benzothiadiazine 1,1-dioxides, a 3-acetyl-2-methyl derivative was synthesized. Attempted reduction of the 3-acetyl moiety to an ethyl group with LiAlH4 led surprisingly to the corresponding 2,3-dihydro-1,2-benzisothiazol 1,1-dioxide, a ring-contracted product. The possible mechanisms of this new, base-mediated rearrangement reaction are discussed. The reaction conditions were optimized by using various bases, and the rearrangement reaction was extended to compounds exhibiting various substituents at the 4-position of the benzothiadiazine ring system.
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