New Versatile Route to the Synthesis of Tetrahydro-β-carbolines and Tetrahydro-pyrano[3,4-<i>b</i>]indoles via an Intramolecular Michael Addition Catalyzed by InBr₃

Abstract

A simple multistep synthetic strategy to 4-substituted 1,2,3,4-tetrahydro-beta-carboline and 1,3,4,9-tetrahydro-pyrano[3,4-b]indole derivatives starting from commercially available indole 2-carboxylic acid (5) is described. The final intramolecular Michael addition promoted by catalytic amount of InBr(3) (5-10 mol %) provided the expected polycyclic compounds in excellent yields (up to 97%) both in anhydrous organic and aqueous media.