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Paper | Regular issue | Vol 81, No. 3, 2010, pp.637-648
Published online, 18th January, 2010
DOI: 10.3987/COM-09-11884
■ Iodotrimethylsilane and Catalytic Iodine Promoted Cyclization for the Facile Synthesis of 3-Monoarylated Five-Membered Benzosultams

Yue-Hui Dong, Qiong-Wei Ni, Shu-Tao Ma, and Zhao-Peng Liu*

*Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44, WenHua XiLu, Jinan 250012, China

Abstract

3-Monoarylated five-membered benzosultams with various functional groups were prepared by simple and convenient two-step procedures. N-t-Bu-benzenesulfonamides were lithiated and reacted with substituted aromatic aldehydes to form the corresponding carbinols, which were converted to the cyclic compounds via a sequence of consecutive processes mediated by TMSCl-NaI-MeCN reagent and catalytic amount of iodine. Iodine played a crucial role in the eliminating the reductive side reaction in the cyclization processes.