INTRAMOLECULAR DIELS-ALDER REACTION WITH FURANS - EFFECT OF THE SUBSTITUTION PATTERN REINVESTIGATED

Intramolecular Diels-Alder reactions occurred smoothly when N-(alpha-c yanofurfuryl)arylamines 2a-g and N-furfurylarylamines 7a-d were treate d with maleic anhydride and fumaroyl chloride-triethylamine respective ly, to afford the corresponding cycloadducts 4 and 10 in good yields. Electron-withdrawing groups and the cyano group inhibited the IMDA rea ction 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.