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.
Current Organic Chemistry
Title:Cu(II) Mediated Chalcone Synthesis via α-bromocarbonyl Intermediate: A One-Step Synthesis of Echinatin
Volume: 21 Issue: 7
Author(s): Jung-hun Lee, Dae-Youn Jeong, Seung-Young Jung, Sukchan Lee, Kye W. Park and Jin-Mo Ku
Affiliation:
Keywords: Aldol condensation, Cu(II) catalysis, polyhydroxy chalcones, echinatin, one-step synthesis.
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.
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Cite this article as:
Lee Jung-hun, Jeong Dae-Youn, Jung Seung-Young, Lee Sukchan, Park W. Kye and Ku Jin-Mo, Cu(II) Mediated Chalcone Synthesis via α-bromocarbonyl Intermediate: A One-Step Synthesis of Echinatin, Current Organic Chemistry 2017; 21 (7) . https://dx.doi.org/10.2174/1385272821666161216102008
DOI https://dx.doi.org/10.2174/1385272821666161216102008 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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