Intramolecular Diels–Alder reaction with furans: effect of the substitution pattern reinvestigated
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1197-1200
- https://doi.org/10.1039/p19930001197
Abstract
Intramolecular Diels–Alder reactions occurred smoothly when N-(α-cyanofurfuryl)arylamines 2a–g and N-furfurylarylamines 7a–d were treated with maleic anhydride and fumaroyl chloridetriethylamine respectively, to afford the corresponding cycloadducts 4 and 10 in good yields. Electron-withdrawing groups and the cyano group inhibited the IMDA reaction when a less activated dienophile was employed. The structures of these IMDA products were fully characterised on the basis of spectral results and elemental analyses.Keywords
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