Studies on Quinoline and Isoquinoline Derivatives. IX. Synthesis of Pyrrolo [1, 2-b] isoquinolines from 3-Bromoisoquinoline Derivatives

Abstract

The reaction of 3-bromo-1-methoxyisoquinoline with propargyl alcohol in the presence of dichlorobis (triphenylphosphine) palladium and cuprous iodide gave 3-(1-methoxy-3-isoquinolyl) propargyl alcohol in good yield. Cyclization of 3-(1-methoxy-3-isoquinolyl) propanol obtained by the catalytic reduction of the propargyl alcohol, afforded a 1, 2, 3, 5-tetrahydropyrrolo [1, 2-b] isoquinoline derivative. The synthesis of a pyrrolo [3, 2, 1-de] phenanthridine derivative was accomplished by the introduction of an acrylic acid moiety into the pyrrolo [1, 2-b] isoquinoline and subsequent reduction and cyclization of the resulting ethyl pyrrolo [1, 2-b] isoquinoline-10-acrylate.