No abstract

Various 3,4-disubstituted indoles were prepared from 4-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline which was obtained readily by the two novel synthetic routes starting from 2-methyl-5-nitroisoquinolinium iodide.

Die Oxazepine (I) bilden bei der Es Strahlung die Formylindole (II).

Durch Reduktion des Isochjnoliniumiodids (I) mit Natriumborhydrid erhält man in 90%iger Ausbeute ein 3:1‐Gemisch aus Dihydro‐ (II) und Tetrahydro‐isochinolin (III), das bei der Vilsmeyer‐Reaktion zum Aldehyd (IV) (48% Gesamtausbeute, bezogen auf (I)) und zum Nebenprodukt (V) (15%) führt.

A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting in the improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine, a potent anti-dormant mycobacterial agent.