A novel set of functionalized dibenzo[c,f]thiazolo[3,2-a]azepines, which is a new ring system, were successfully synthesized in a four-step protocol starting from readily available substituted N-allyl-N-benzylanilines. The synthesis of the title compounds was accomplished through cyclocondensation of morphanthridines with mercaptoacetic acid. Morphanthridines were prepared by selective oxidation of dihydromorphanthridines with pyridinium chlorochromate in dichloromethane. The dihydromorphanthridines were obtained by acid-catalyzed intramolecular Friedel-Crafts alkylation of substituted 2-allyl-N-benzylanilines, which in turn, were prepared from N-allyl-N-benzylanilines by aromatic amino-Claisen rearrangement. The structural elucidation of all synthesized compounds by high resolution NMR is also reported.