Naphtho[2’,1’,6,7]oxepino[3,4-b]quinolin-7(14H)-one (3a) and naphtho[1’,2’,6,7]oxepino[3,4-
b]quinolin-15(8H)-one (3b) were synthesized by the intramolecular Friedel-Crafts acylation reactions of 2-[(naphthalen-1-yloxy)methyl]quinoline-3-carboxylic acid (2a) and 2-[(naphthalen-2-yloxy)methyl]-
quinoline-3-carboxylic acid (2b) under the treatment of Eaton’s reagent (P2O5-MeSO3). Compounds 2a and 2b were prepared by a one-pot method of ethyl 2-(bromomethyl)quinoline-3-carboxylate (1) with α-naphthol and β-naphthol, respectively. The synthesized compounds 3a and 3b could be further treated with potassium hydroxide in 60% (V/V) ethanol-water solution to undergo 1,2-Wittig rearrangement and atmospheric oxida-tion reactions to afford naphtho[2,1-b] acridine-7,14-dione (4a) and naphtho[1,2-b]acridine-7,14-dione (4b). The structures of 2a～4a and 2b～4b were confirmed by IR, UV, 1H NMR, MS techniques and elemental analysis. The UV-vis spectra of 2a～4a and 2b～4b measured in trichloromethane showed that the maxi-mum absorption peaks were at 280, 261, 312, 273, 256 and 313 nm, respectively. The fluorescence emission spectra of 3a, 4a and 3b, 4b in the solid state showed that the maximum emission wavelengths were at 350, 300, 274 and 330 nm, respectively.

Key words: Eaton’s reagent, naphthooxepinoquinolinone, naphthoacridinedione, 1,2-Wittig rearrangment, fluorescence, one-pot