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Paper | Regular issue | Vol 51, No. 1, 1999, pp.103-117
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8362
A Novel Synthesis of Isoquinolines Containing an Electron Withdrawing Substituent

Harumichi Kohno and Koichiro Yamada*

*Medicinal Chemistry Research Laboratory, Tanabe Seiyaku Co.Ltd.,, 2-2-50, Kawagishi, Toddda, Saitama 335-8505, Japan

Abstract

3,4-Dihydroisoquinolines (10, 13) and isoquinolines (11), having various electron withdrawing substituent were synthesized in two steps from N-benzenesulfonyl- or N,N-dimethylsulfamoyl-β-phenethylamines (2 and 5). A novel cyclization method using ethyl chloro(methylthio)acetate (1) in the presence of SnCl4 as Lewis acid, followed by acid or base treatment provides the title compounds in good yield.