Rare and highly medicinally relevant N-alkoxy-substituted benzo[1,4]oxazepines have been synthesized conveniently via the base-promoted SNAr/Smiles rearrangement/SNAr tandem cyclization of N-alkoxysalicylamides with a range of bis-electrophilic substrates; subsequent de-alkylation gives rise to the respective N-hydroxy versions. The compounds reported herein significantly add to the contemporary arsenal of small molecule tools for drug discovery. (C) 2016 Elsevier Ltd. All rights reserved.