Synthesis of N(2)-Hydroxy-1,2,3,4-tetrahydro-b-carbolines

Abstract

N-Hydroxytryptamine condensed readily with a series of aldehydes in the presence of a catalytic amount of acetic acid to give the corresponding nitrones (%a-f), which in turn were cyclired by hydrochloric acid to the stable N(2)-hydroxytetrahydro-6carbolines (5a-f).-8-Carbolines of this type have not previously been synthesized, and are of interest because of their structural relationship to several potent antiviral marine alkaloids (eudistomins C, E, K and L).