Session: Heterocycles & Aromatics:

The readily available and bench stable tricarbonyl(tropone)iron complex is demonstrated to be a versatile starting material for the synthesis of different azapolycyclic skeletons containing seven-membered carbocyclic rings. This approach involves an aza-Michael reaction of an amine to tricarbonyl(tropone)iron to forge the key C–N bond. Depending on the functionality present on the amine nucleophile's side chain, different C–C bond forming reactions can be performed to forge different polycycles. In this work, we demonstrate that: 1) allylamine can be added to the tropone ligand and participate in an intramolecular Diels-Alder reaction following demetallation to form a novel azatricycle; 2) 2-bromoprop-2-en-1-amine can be similarly added and then participate in an intramolecular Heck cyclization following demetallation to form an alternate bridged azabicycle.

Prof. Daniel R. Griffith

Assistant Professor, Lafayette College

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