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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 | Source: | 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. | Document URI: | http://hdl.handle.net/1942/4394 | DOI: | 10.1039/P19910000639 | Type: | Journal Contribution |
Appears in Collections: | Research publications |
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