The literature on the syntheses of substituted 1-(indol-3-yl)-1,2,3,4-tetrahydroisoquinoline
derivatives is reviewed. Two main synthetic procedures have been applied for
these syntheses. One is cross-dehydrogenative coupling, which can furnish various C-3 functionalized
indoles; oxidants and/or catalysts are usually needed. Another convenient synthetic
method is the aza-Friedel–Crafts alkylation of indole derivatives with dihydroisoquinoline,
the main advantage of this being the direct catalyst-free coupling under mild experimental
conditions. The review also considers miscellaneous reactions, where the isoquinoline
skeleton is achieved in one of the final steps of the synthesis.
Keywords: Isoquinoline, indole, β-carboline, cross-dehydrogenative coupling, aza-Friedel–Crafts alkylation.
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