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Intramolecular Diels–Alder Reaction With Furans: Effect Of The Substitution Pattern Reinvestigated

D. Prajapati, D. Borthakur, J. S. Sandhu
Published 1993 · Chemistry

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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.
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