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Original Article

ECB. 2013; 2(11): 898-903


SYNTHESIS OF RING FUSED CYCLIC KETONES VIA DOMINO FRIEDEL-CRAFTS REACTIONS OF FUNCTIONALIZED 5- MEMBERED HETEROCYCLIC PERCHLORATES

Mahmoud R. Mahmoud, Hamed A. Derbala, Hassan M. F. Madkour, Naglaa F. El-Said.




Abstract

Z-4-(Naphth-2-ylmethylene)-2-phenyloxazol-5(4H)-one and 3-(phenylcarbamoyl)but-3-enoic acid 2 and 5, respectively, are readily
transformed into the corresponding perchlorate salts 3 and 6 with acetic anhydride-perchloric acid mixture. Conduct the latter salts with
arenes in the presence of anhydrous AlCl3 provided novel derivatives of benzo[g]indenones 7 and 1-tetralones 8, respectively, via two
consecutive Friedel-Crafts reaction in situ. The structure of all the synthesized products was characterized using IR, 1H NMR, 13C NMR
and mass spectra.

Key words: Oxazolonium perchlorates, Indanones, Domino Friedel-Crafts






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