An efficient protocol for the synthesis of novel fused N-heteropolycycles 10a-f (tetracyclic-fused and bridged dibenzo-azepinone,-azocinones,-azoninone, benzo [b] pyrido [3, 2-f] azocinone and benzo [c] pyrido [3, 2-g] azoninones) via combined Darzens and Friedel-Crafts methodologies is described. The starting ketones 5a, b were conveniently obtained via cyanoethylation of aminoxylenes 1a, b followed by hydrolysis of the resulting nitriles 3a, b to the corresponding carboxylic acids 4a, b and were finally acylated by intramolecular Friedel-Crafts reaction. The key acetylated intermediates 7a, b were obtained by Darzens condensation. Subsequently, two steps led to substituted heterocyclic acids 9a-f which successfully underwent Friedel–Crafts cycloacylations mediated by AlCl3/CH3NO2, TfOH or P2O5 catalysts. The method offers readily access to diverse drug-like 10a-f scaffolds in moderate to good yields. a: n= 0, x= 0, Y= CH; b: n= 0, x= 1, Y= CH; c: n= 0, x= 1, Y= N; d: n= 1, x= 0, Y= CH; e: n= 1, x= 1, Y= CH; f: n= 1, x= 1, Y= N