Chemical and pharmaceutical bulletin

An Improved Synthesis of 1, 2, 3, 4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl) methyl-2-(phenylsulfinyl) ethylamine by Pummerer …

T Shinohara, J Toda, T Sano

Index: Shinohara, Tatsumi; Toda, Jun; Sano, Takehiro Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 5 p. 813 - 819

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Citation Number: 34

Abstract

Pummerer reaction of the sulfoxides 5 of N-acyl-N-(aryl) methyl-2-(phenylthio) ethylamines (4) on treatment with trifluoroacetic anhydride (TFAA) effectively caused intramolecular cyclization under a mild condition to give N-acyl-4-phenylthio-1, 2, 3, 4- tetrahydroisoquinolines (TIQs)(7). The reaction of the N-formyl sulfoxide 5c without a methoxy group in the benzene ring using a formyl group for N-protection is particularly ...