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Communication | Special issue | Vol 42, No. 1, 1996, pp.141-144
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S47
A Novel Cyclization of Electron Deficient N-Benzenesulfonyl-β-phenethylamines Using Ethyl Chloro(methylthio)acetate. Synthesis of Ethyl 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates

Harumichi Kohno and Yasuo Sekine

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

Abstract

The reaction of electron deficient N-benzenesufonyl-β-phenethylamines (2) with ethyl chloro(methylthio)acetate (1) gave ethyl 2-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylates (3) in high yields. We examined the effects of a substituent on the benzene ring and several Lewis acids in this cyclization.