A facile and convenient method for fluorine-containing Benz[c]acrindines and dihydrobenz[c]acridines from N,N-dimethyl-1-naphthylamine

Aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (1) with p-substituted anilines gives the corresponding N-aryl-2,4-bis(trifluoroacetyl)-1-naphthylamines 2 in high yield. Acid-catalyzed cyclization of 2 affords selectively fluorine-containing benz[c]acridines 3 in almost quantitative yield, while the base-catalyzed cyclization gives fluorine-containing 7,12-dihydrobenz[c]acridines 4 in fair yield