Efficient and concise protocol for the synthesis of fused tetracyclic N,S-heterocycles in particular benzo-and pyrido-fused 1,4-thiazonines, 1,4-thiazecines and 1,4-thiazacycloundecanes is described. The process involves Lewis or Brønsted acids-promoted Friedel-Crafts cyclizations of heterocyclic esters. The required starting thiazepinones were obtained in moderate yields via intramolecular thio-Michael additions of mercaptoamides under mild conditions. The present study without stereochemical assignments illustrates the first example of straightforward access to promising pharmaceutical scaffolds in high yields.