Abstract
Background: Since introduction of chalcones in 1899, chalcones have been considered as precursors of flavones in the biosynthesis of flavonoids. However, because the chalcones include multi-functional groups on aromatic rings, developments of efficient synthetic methodologies as well as synthetic strategies involving protection/ deprotection should be considered.
Objective: The primary objective of this study was to describe chalcone synthesis under mild condition and its mechanism study.
Method: The chalcones synthesis is aldol condensation of acetophenones with aldehydes in the presence of catalytic mount of copper(II) bromide at 70 °C.
Result: Proposed transformation of the chalcone synthesis is to proceed via catalytically generated abromocarbonyl intermediate by copper(II) bromide, aldol condensation of a-bromocarbonyl intermediate is promoted by HBr, while its byproducts, HOBr and HBr reconstitute the catalyst. Using this method, the natural product echinatin (1) was conveniently synthesized in a single step with yield of 82%.
Conclusion: Cu(II) mediated aldol condensation via a-bromocarbonyl species involving Cu(II) catalyst reconstitution were noted in this study. It was thought that it has the potential for application as a simple and quick synthesis method for pharmaceutical ingredients.
Keywords: Aldol condensation, Cu(II) catalysis, polyhydroxy chalcones, echinatin, one-step synthesis.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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