Structure, reactivity, and application of some triketone derivatives

The major tautomer of several triketone derivatives in organic and aqueous solutions has been determined. Their solvent- and base-sensitive properties have been applied in the design of a polarity-sensitive fluorescent probe and an acidichromic colorant, respectively. The regioselective acetylation and methylation of 2-acyldimedone, 3-acyl-4-hydroxycoumarin, and 2-acyl-1,3-indandione have also been investigated. The results indicated that acetylation and methylation of the first two occurred specifically at endocyclic enolic oxygens, whereas for the latter they occurred at exocyclic enolic oxygen. (c) 2006 Elsevier Ltd. All rights reserved.