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Title: An exploratory study on microwave-assisted solid-phase Diels-Alder reactions of 2(1H)-pyrazinones: the elaboration of a new tailor-made acid-labile linker
Authors: Kaval, Nadzeya ×
Van der Eycken, J
Caroen, J
Dehaen, Wim
Strohmeier, GA
Kappe, CO
Van der Eycken, Erik #
Issue Date: Jan-2003
Publisher: Amer chemical soc
Series Title: Journal of combinatorial chemistry vol:5 issue:5 pages:560-568
Abstract: Microwave-assisted solid-phase Diels-Alder cycloaddition reactions of 2(1H)-pyrazinones with dienophiles are discussed. Separation of the resulting pyridines from the pyridinone byproducts was achieved by applying a traceless-linking concept, whereby the pyridinones remain on the solid support with concomitant release of the pyridine products to solution. As a model study, Wang linker was mimicked in solution using a 4-methoxybenzyl group at the N1 position of the 2(1H)-pyrazinone. The sequence was successfully carried out in solution under conventional thermal heating conditions as well as utilizing high-speed microwave irradiation. The results were adapted to polystyrene supports, using various different acid labile linkers, such as Wang resin, HMPB-AM resin, and a novel, tailor-made acid-labile linker based on syringaldehyde, which has been proven in terms of cleavage rates to be superior to both the standard Wang and HMPB-AM linkers. All steps in the solid-phase protocol (linking, cycloaddition, cleavage) were carried out under both thermal and controlled microwave irradiation conditions. In general, significant rate enhancements were found for reactions carried out under high-temperature microwave conditions, reducing reaction times from hours or days to minutes.
ISSN: 1520-4766
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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