Carbolines comprise a specific class of heterocyclic aromatic amine.  Previous studies have established the biological activity of these molecules to include cytotoxicity against certain cancer cell lines and bacterial strains.  We have recently reported a novel five step synthesis of a 3,4-annulated  β-carboline via an intramolecular [2+2+2] cyclization strategy starting with commercially available iodoaniline.  Hoping to expand the scope of this scheme, our goal is to synthesize a library of analogues with the same annulation at the 3,4 position but with different substitution patterns on the iodoaniline.  By adding both electron withdrawing and electron donating groups on the ortho-, meta-, and para-positions, we can demonstrate the generality of our synthetic technique.  Our results indicate good to excellent yields for the following groups: 3-Cl, 4-Cl, 4-F, 4-CO<sub>2</sub>Me, 4-Me, and 4-OMe, which has allowed us to understand the electronic requirements of the [2+2+2] reaction.

Electronic effects of intramolecular [2+2+2] cyclizations toward β-carbolines

249th National Meeting (2015)

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