Abstract Syntheses of several 6, 6, 6-tricyclic condensed pyridines and pyrazines utilizing intramolecular Diels-Alder reactions of 1, 2, 4-triazines with alkyne and nitrile dienophiles are detailed. The cyclizations are facilitated by the presence of conformationally restrictive planar aromatic rings in the chain tethering the diene and the dienophile.