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Paper | Regular issue | Vol 31, No. 2, 1990, pp.341-351
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5247
Synthesis of Aromatic Chloroberbines

Georges Memetzidis, Jean-françois Stambach,* and Louis Jung

*Laboratoire de Chimie Thérapeutique, U.F.R. des Sciences Pharmaceutiques, Université Louis Pasteur, 74, route du Rhin, BP 24, 67401 ILLKIRCH Cedex, France

Abstract

The introduction of chlorine atoms into aromatic rings of berbines was effected from an ethoxycarbamido group which does not undergo decomposition under the conditions of the Bischler-Napieralski reaction. At the end of he synthesis of the berbine ring system this group was transformed into a primary aromatic amine which was converted into chlorine by the Sandmeyer reaction. Thus berbines 6a,b chlorinated in the aromatic ring A and berbines 10a,b chlorinated in the aromatic ring D were prepared. The preparation of the starting β-phenethylamines 1a,b with an ethoxycarbamido group was also discussed.