Abstract
The indolo[2,1- a]isoquinoline and pyrrolo[2,1- a]isoquinoline nuclei have been synthesized from N-benzylindole or ethyl 1 H-indol-1-ylacetate and N-benzylpyrrole precursors, respectively. Firstly, at C-2 of either the indole or pyrrole nucleus, aromatic rings containing a carbonyl substituent ortho to the newly formed biaryl axis were introduced using the Suzuki–Miyaura coupling reaction. Thereafter, under basic conditions the nucleophile that formed at the acidic methylene protons of the N-benzylindole, ethyl 1 H-indol-1-ylacetate or N-benzylpyrrole intermediate reacted with the internal aromatic carbonyl to yield (after the expulsion of water) the title compounds. For example, exposure of ethyl 2-(2-(2-formylphenyl)-1 H-indol-1-yl)acetate to potassium tert-butoxide resulted in the formation of ethyl indolo[2,1- a]isoquinoline-6-carboxylate.
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