An unprecedented [4 + 3] annulation reaction of aza- ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1 H-benzo[ e][1,2,4]triazepine.