Cu(II) Mediated Chalcone Synthesis via α-bromocarbonyl Intermediate: A One-Step Synthesis of Echinatin

Author(s): Jung-hun Lee, Dae-Youn Jeong, Seung-Young Jung, Sukchan Lee, Kye W. Park, Jin-Mo Ku.

Journal Name: Current Organic Chemistry

Volume 21 , Issue 7 , 2017

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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.

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Article Details

VOLUME: 21
ISSUE: 7
Year: 2017
Page: [652 - 658]
Pages: 7
DOI: 10.2174/1385272821666161216102008
Price: $58

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