The interaction of peri-dilithionaphthalenes with organic cyanides was studied. Instead of the expected peri-diimines, the reaction leads to the formation of three types of benzo[ de]isoquinolines. Treatment of unsubstituted 1,8-dilithionaphthalene with aromatic nitriles results in the formation of 1-amino-1,3-diaryl-1 H-benzo[ de]isoquinolines. In contrast, 4,5-dilithio-1,8-bis(dimethylamino)naphthalene gives an aromatic isoquinolonium cation via elimination of ammonia under the same condition. Upon treatment with tert-butylcyanide, both dilithionaphthalenes undergo a transformation to 1-amino-3,4-di- tert-butyl-4 H-benzo[ de]isoquinolines. The observed reactivity was supported by quantum chemical calculations.

Original languageEnglish
Pages (from-to)977-981
Number of pages5
JournalOrganic Letters
Volume25
Issue number6
DOIs
StatePublished - 17 Feb 2023

ID: 105207153