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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/4394

Title: Smooth generation of 3H-2-benzopyron-3-ones and their Diels-Alder reactions with olefinic dienophiles
Authors: van Broek, P.I.
VANDERZANDE, Dirk
Kieckens, Eric G.
Hoornaert, G.J.
Issue Date: 1991
Citation: Journal of the Chemical Society: Perkin transactions I. p. 639-644
Abstract: The generation of methoxy-substituted 3H-2-benzopyran-3-ones from o-acylphenylacetic acid derivatives in acetic anhydride at 140 °C and their in situ Diets–Alder reactions being inefficient in the synthesis of some carbocyclic compounds, alternative reagents have been used. It is shown that, e.g. 1,3-dicyclohexylcarbodiimide (DCC) with 2-hydroxypyridine, disuccinimidyl carbonate (DSC), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) of 2-isobutoxy-N-isobutoxycarbonyl-1,2-dihydroquinoline (IIDQ) are much more efficient reagents.Using these alternative reagents the formation of side-products from the benzopyranone, e.g. chrysene, can be avoided; with the modified DCC-method the 6,7-dimethoxy-1 -methyl-2-benzopyran3-one intermediate 8a can be identified spectroscopically. An exemplified procedure with IIDQ is proposed, opening new prespectives for Diets–Alder reactions of unstable or less reactive dienophiles with problematic benzopyranones.
URI: http://hdl.handle.net/1942/4394
DOI: 10.1039/P19910000639
Type: Journal Contribution
Appears in Collections: Research publications

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