Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds: Ligands of the Aryl Hydrocarbon Receptor

Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla

By engaging indole aldehydes in an isocyanide multicomponent reaction, the polarity inversion of the indole moiety along the transformation triggers an extension of the domino process, leading to a variety of unprecedented fused, linked, and bridged scaffolds. The processes can be run in parallel and the adducts display remarkable bioactivity as potent ligands of the aryl hydrocarbon receptor.