Novel, one-pot synthesis of benz-[g]-indenones and 1-tetralones from functionalized 5-membered heterocyclic perchlorates via domino friedel-crafts reactions

Abstract

(Z)-4-(Naphth-2-ylmethylene)-2-phenyloxazol-5(4H)-one 1 and 3-(phenylcarbamoyl)-but-3-enoic acid and 3, respectively, are readily transformed into their corresponding perchlorate salts 2 and 4 with acetic anhydrideperchloric acid mixture. Conducting the latter salts with arenes in the presence of AlCl3 provided novel derivatives of benz-[g]-indenones 5 and 1-tetralones 6, respectively, via two consecutive Friedel-Crafts reactions in situ. The structures of all the synthesized products were characterized using IR, 1H NMR, 13C NMR, and mass spectra.