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Short Paper | Regular issue | Vol 85, No. 3, 2012, pp.667-676
Published online, 26th January, 2012
DOI: 10.3987/COM-11-12411
A Novel Solid-Phase Synthesis of Quinolines

E Tang,* Deshou Mao, Wen Li, Zhangyong Gao, and Pengfei Yao

*School of Chemical Science and Technology, Yunnan University, No. 2 Green Lake North Road, Kunming 650091, China

Abstract

A method for synthesizing substituted-quinolines using TMSOTf-catalyzed polystyrene-supported succinimidyl selenide-induced intramolecular seleno-arylation of tethered alkenes as a key step has been developed. The catalytic process provides an efficient method for the stereoselective and regioselective synthesis of tetrahydroquinoline possessing a seleno-functionality, followed by deprotection of tosyl group and syn-elimination of selenoxides to provide quinolines in good yields and purities.