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Accessing highly-halogenated flavanones using protic ionic liquids and microwave irradiation

Thornton, Megan T., Henderson, Luke C., Byrne, Nolene and Pfeffer, Frederick M. 2012, Accessing highly-halogenated flavanones using protic ionic liquids and microwave irradiation, Current organic chemistry, vol. 16, no. 1, pp. 121-126.

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Title Accessing highly-halogenated flavanones using protic ionic liquids and microwave irradiation
Author(s) Thornton, Megan T.
Henderson, Luke C.
Byrne, Nolene
Pfeffer, Frederick M.
Journal name Current organic chemistry
Volume number 16
Issue number 1
Start page 121
End page 126
Total pages 6
Publisher Bentham Science Publishers Ltd
Place of publication Bussum, Netherlands
Publication date 2012-01
ISSN 1385-2728
Keyword(s) chalcone
claisen-schmidt
flavanone
hydroxyacetophenone
microwave
protic ionic liquid
microwave-assisted chalcone
chalcone synthesis
thin layer chromatography (TLC)
column chromatography
protic ionic liquids (pILs)
EAN (ethylamine:nitric acid)
TeaMs (triethylamine:methanesulfonic acid)
proton activity
Summary 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.
Language eng
Field of Research 030503 Organic Chemical Synthesis
030504 Organic Green Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2012, Bentham Science Publishers
Persistent URL http://hdl.handle.net/10536/DRO/DU:30046961

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Created: Mon, 13 Aug 2012, 12:54:32 EST