A tandem approach to (hetero)arene-fused benzo[f]imidazo[1,2-d][1,4]oxazepines has been described which involves condensation of bis-nucleophilic 2-(2-hydrohyaryl)imidazoles with reactivity-matched o-dihalo and o-halonitro (hetero)aromatic substrates. The process is generally regioselective with respect to the unsymmetrically substituted imidazole ring and proceeds via two S_NAr events (intermolecular first and then intramolecular) intermitted by a Smiles rearrangement. In some cases, the last S_NAr step provides a rare example of nucleophilic displacement of a nitro group or a halogen in non-activated positions of a (hetero)aromatic ring which does not require the use of a metal catalyst.