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Communication | Regular issue | Vol 24, No. 9, 1986, pp.2407-2410
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2407
One Pot Preparation of 1,3-Dimethyltetrahydroisoquinolines from Their Biosynthetic Diketo Precursors

Gerhard Bringmann* and Johannes R. Jansen

*Organisch-Chemisches Institut, Universität Münster, Orleansring 23, D-4400 Münster, Germany

Abstract

Biomimetic reactions modelling the nitrogen incorporation into the monocyclic precursors 2 of naphthylisoquinoline alkaloids, using pyridoxamine (9b) are described. The condensation of 2b with 9b, or, more simply, with benzylamine, though not giving a dihydroisoquinoline 7, provides an efficient one pot synthesis of already protected 1,3-dimethyltetrahydroisoquinolines 14, by in situ reduction of the resulting isoquinolinium salts 12.