A one‐pot four‐component synthesis of 6‐aryl‐6H‐dibenzo[e,i][1,3,7,2]oxadiazaborecin‐8(7H)‐ones is described. Heating a mixture of isatoic anhydride and a benzylamine afforded the corresponding anthranilamide derivative, which was condensed with a 2‐hydroxybenzaldehyde and an arylboronic acid under solvent‐free conditions to produce bridgehead bicyclo[4.4.0]‐boron heterocycles in good to excellent yields. Single‐crystal X‐ray analysis conclusively confirms the structures of the obtained bridgehead bicyclic 6–6 heterocyclic compounds.