The low aromaticity of furan allows it to participate in reactions that destroy the conjugation of the ring, such as: Diels-Alder, 1,3-dipolar, photochemical and kelotropic.

furan cycloaddition reactions

d) Chelotropics.

furan cycloaddition reactions 02

The much more aromatic pyrrole does not give these reactions, but it is possible to decrease its aromaticity with electron-withdrawing groups on the nitrogen atom.

furan cycloaddition reactions 03