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The 2-C,methylene group of 1-aroyl-1,2-dihydro-3H-naphtho[2,1-b]pyran-3-ones(2)have been showed to possess a superior reactivity towards many of organic reagents.The na-phthopyrones(2)condensed with aromatic aldehydes to give the 2-arylidine derivatives(3).Bromin-ation of 2 gave 1,2-dibromo(4)or 5-bromo(5)derivatives depending on the reaction conditions.The base catalyzed addition or cycloaddition of naphthopyrones(2)to 4-methoxy benzalacetophenonegave the expected Michael adduct(6)or the cyclic adducts(7-9)depending on the type of catalyticbase and reaction conditions.Structures of the products have been established by elemental analyses,IR and ~1H NMR spectroscopic methods.