The First Synthesis of Bis(arylmethylidene)dioxan-5-ones: Potential Scaffolds to Access Vicinal Tricarbonyl Derivatives

Abstract

Double crossed-aldol condensation of a variety of aromatic aldehydes with 1,3-dioxan-5-one in the presence of magnesium bromide diethyl etherate and diethylamine at room temperature is described. Excellent yields of 4,6-bis(arylmethylidene)dioxan-5-ones are achieved in a facile, one-pot, general procedure. The structure and the Z,Z-configuration of the exocyclic double bonds of the products were determined by spectroscopic methods and X-ray crystallography, respectively.

Key words

dioxanone - aldol condensation - MgBr₂·Et₂O - hetero­cycles

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For an updated list of references on the preparation and synthetic applications of these compounds, see references 14-18 and references therein.