One Pot Preparation of 1,3-Dimethyltetrahydroisoquinolines from Their Biosynthetic Diketo Precursors

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Abstract
Biomimetic reactions modelling the nitrogen incorporation into the monocylic 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.
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