Abstract
A series of highly-functionalized 2-hydroxychalcones have been synthesized using a microwave-assisted Claisen-Schmidt condensation. Conversion of these 2-hydroxychalcones to their corresponding flavanones was then performed utilizing protic ionic liquids (pIL) and microwave irradiation. This methodology drastically reduces reaction time to 15 minutes compared to typical thermal methods (24 hrs) and is tolerant to a broad range of functional groups. Several chalcones reported bear four and five substituents - a degree of substitution rarely reported in the literature.
Keywords: Chalcone, Claisen-Schmidt, Flavanone, Hydroxyacetophenone, Microwave, Protic Ionic Liquid, Microwave-assisted chalcone, Protic ionic liquids, chalcone synthesis, Thin layer chromatography (TLC), Column Chromatography, Protic ionic liquids (pILs), EAN (ethylamine:nitric acid), TeaMs (triethylamine:methanesulfonic acid), proton activity
Current Organic Chemistry
Title: Accessing Highly-Halogenated Flavanones Using Protic Ionic Liquids and Microwave Irradiation
Volume: 16 Issue: 1
Author(s): Megan T. Thornton, Luke C. Henderson, Nolene Byrne and Frederick M. Pfeffer
Affiliation:
Keywords: Chalcone, Claisen-Schmidt, Flavanone, Hydroxyacetophenone, Microwave, Protic Ionic Liquid, Microwave-assisted chalcone, Protic ionic liquids, chalcone synthesis, Thin layer chromatography (TLC), Column Chromatography, Protic ionic liquids (pILs), EAN (ethylamine:nitric acid), TeaMs (triethylamine:methanesulfonic acid), proton activity
Abstract: A series of highly-functionalized 2-hydroxychalcones have been synthesized using a microwave-assisted Claisen-Schmidt condensation. Conversion of these 2-hydroxychalcones to their corresponding flavanones was then performed utilizing protic ionic liquids (pIL) and microwave irradiation. This methodology drastically reduces reaction time to 15 minutes compared to typical thermal methods (24 hrs) and is tolerant to a broad range of functional groups. Several chalcones reported bear four and five substituents - a degree of substitution rarely reported in the literature.
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Cite this article as:
T. Thornton Megan, C. Henderson Luke, Byrne Nolene and M. Pfeffer Frederick, Accessing Highly-Halogenated Flavanones Using Protic Ionic Liquids and Microwave Irradiation, Current Organic Chemistry 2012; 16 (1) . https://dx.doi.org/10.2174/138527212798993167
DOI https://dx.doi.org/10.2174/138527212798993167 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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