Graphical abstract: Abstract: A general approach to the synthesis of ( E )-5-(substituted) benzylidene-2, 3, 4, 5-tetrahydro-1 H -azocino[5, 4- b ]indol-6(7 H )-ones via intramolecular Friedel Craft's reaction of allylamines prepared from tryptamine and allyl bromides is reported.