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Paper | Regular issue | Vol 81, No. 2, 2010, pp.317-327
Published online, 16th November, 2009
DOI: 10.3987/COM-09-11858
One-Pot Aryl-1,4-thiomorpholine 1,1-Dioxide Synthesis via Double 1,4-Addition of in situ Reduced Nitroarenes to Divinyl Sulfones

Joon Hee Han, Jaehwan Choi, Young Moo Jun, Byung Min Lee, and Byeong Hyo Kim*

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea


One-pot reduction-triggered double aza-Michael type 1,4-addition reactions of various nitroarenes to divinyl sulfones were investigated. In the presence of indium/AcOH in MeOH or in sat. aq NH4Cl/MeOH, nitroarenes and divinyl sulfones were cyclized to give 1,4-thiomorpholine 1,1-dioxides.