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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2377-2388
Published online, 3rd August, 2007
DOI: 10.3987/COM-07-11120
Novel Method for the Synthesis of 3-Monosubstituted Six-Membered Benzosultams

Fang Fang, Rui Wang, Zhao-Peng Liu,* and Ai-Guo Ji

*Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P.R. China

Abstract

3-Monosubstituted six-membered benzosultams with a wide range of functional groups were prepared by simple and convenient two-step procedures. o-Lithiation of N-Boc-o-toluenesulfonamide followed by reaction with aldehydes gave carbinol sulfonamides, which were converted to 3-monosubstituted six-membered benzosultams via TMSCl/NaI/MeCN reagent mediated cyclization. The mechanism and the scope of this novel transformation are studied.