Condensation of 2,4(3 H ,5 H )-furandione with heteroaromatic aldehydes

2,4(3H,5H)-Furaridione, 1, condenses with heteroaromatic aldehydes in the presence of concentrated hydrochloric acid to yield 3-(heteroarylmethylene)-2,4(3H,5H)-furandiones, 4. The condensation of 1 with acid sensitive aldehydes, including 2-furanacroleine and N-methylpyrrole-2-carboxaldehyde proceeded well with 1 as the sole proton source. The E/Z ratio of type 4 compounds was determined by 1H-nmr spectroscopy.