A protocol involving intramolecular formal [4 + 2]-cycloaddition of in situ generated o-azaquinone methide for the facile synthesis of 1,4heterocycle-fused quinoline motifs is demonstrated. The cascade involved tandem CÀ O, CÀ C, and CÀ N bond formation and also exhibited excellent functional group tolerance. Enantiomerically enriched 1,4-oxazepino quinolines were synthesized using alkynols derived from L-amino acids. The sulfoxide embedded quinolines were transformed to pentacyclic 1,4-thiepino tethered indeno-quinoline scaffolds via Pummerer cyclization.