Scandium(III) Triflate-Catalyzed Reaction of Aroyl-Substituted Donor-Acceptor Cyclopropanes with 1-Naphthylamines: Access to Dibenzo[c,h]acridines.

The reaction of aroyl-substituted donor-acceptor (D-A) cyclopropanes with two equivalents of 1-naphthylamines in the presence of a catalytic amount of scandium(III) triflate provides access to dibenzo[c,h]acridines. The key steps of the transformation are the formation of nucleophilic ring-opening products from the D-A cyclopropanes and 1-naphthylamines and their subsequent fragmentation and cyclization. The method has a reasonable substrate scope, and the products are formed in 50-70% yields.