Diels-Alder reactions of 3-furylamines in organic and aqueous solvents

Various 5-methyl-3-aminofurans have been shown to undergo facile Diels-Alder reactions with methyl acrylate in aqueous media. Reactions proceeded with exclusive regiochemistry, and enamine cycloadducts were readily hydrolyzed to afford 7-oxabicyclo[2.2.1]heptanones in high yields.