The synthesis of 8-Azabenzo[4,5]cyclohepta[1,2,3-de]naphthalene: A new heterocyclic aromatic system

8-Azabenzo[4,5]cyclohepta[1,2,3-de]naphthalene, a nitrogen analogue of one of the hypothetical hydrocarbons on which Pullman et al.1 have made a theoretical-study, has been synthesized. This compound has been found to undergo nucleophilic addition of water, methanol, or aniline to the carbon-nitrogen double bond with surprising ease, and a possible explanation for these reactions has been proposed.