Abstract
We have established formerly that reaction of ethyl 2,4-dibromo-2,4-dimethyl-3-oxopentanoate with zinc and aromatic aldehydes gives rise to previously unknown 6-aryl-3,5,5-trimethyl-2,3,5,6-tetrahydropyran-2,4-diones [1]. It is known that tetrahydropyrandiones with substituents in 3-position containing a carbonyl group possess various kinds of biological activity [234]. Aiming at preparation of new tetrahydropyrandiones types with aroylmethyl group in 3-position of the pyran ring we studied reactions between sodium enolates (II) obtained from 6-aryl3,5,5-trimethyl-2,3,5,6-tetrahydropyran-2,4-diones (I) and para-substituted phenacyl bromides. The investigation established that the reaction between these compounds occurred readily in anhydrous DMSO yielding C-alkylation products of sodium enolates IIa3c, 6-aryl-3-aroylmethyl-3,5,5-trimethyl2,3,5,6-tetrahydropyran-2,4-diones (IIIa3j).
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