Abstract
An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-α,β-unsaturated ketones from aromatic aldehydes and ketones.
Highlights
Chalcones are a very important class of compounds due to their occurrence in Nature and their interesting and versatile pharmacological properties, as summarized in several reviews [1,2,3,4,5]
Chalcones are traditionally accessed by cross-aldol condensations of aryl methyl ketones and aromatic aldehydes in the presence of alkali [16,17,18], a reaction that requires the use of an organic solvent and a highly polluting alkaline base and in most cases needs to be followed by purification by column chromatography, leading
We started our study by examining the model cross aldol condensation reaction between acetophenone (1a) and benzaldehyde (2a) at a relatively large scale (8.6 mmol) in the presence of montmorillonite KSF (MKSF)
Summary
Chalcones (trans-1,3-diaryl-2-propen-1-ones) are a very important class of compounds due to their occurrence in Nature and their interesting and versatile pharmacological properties, as summarized in several reviews [1,2,3,4,5] These properties include antineoplastic [5,6,7], antimalarial [8], antiviral (HIV) [9,10], antibacterial [4,11,12], antioxidant [12] and anti-inflammatory [4,13] activities, among others. Economic and environmental concerns connected to the practice of organic synthesis have received especial attention in recent years In this context, a important area is the development of synthetic processes in the absence of solvents [19,20,21,22]. We present here our studies on a solvent-free protocol for their synthesis under microwave irradiation conditions in the presence of a montmorillonite clay catalyst, its application to a large number of examples in order to establish its scope and a brief study of its subsequent generalization to other types of substrates
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