Abstract
Methyl 5-nitro-2-furylpropiolate was treated with alicyclic secondary amines to obtain the corresponding 5-nitro-2-furyl-β-aminoacrylates in a yield over 50%. Their structures were discussed based on their NMR, IR, and UV spectra. Though such amine-addition products were obtained with diethylamine, phenyl hydrazine, and ammonia, triethylamine, aniline, and N-methylaniline gave a different line of products.
Intramolecular Diels-Alder reactions were attempted using 5-nitro-2-furylpropiolic acid in the presence of acetic anhydride or using its allyl ester. The former afforded only its anhydride, whereas the latter, the desired cyclic product.
