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
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
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
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
64
4