Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation

Summary:

2-furfurylmaleimide (FM) was synthesized and characterized unambiguously for the first time by condensing 2-furfurylamine with maleic anhydride to give the corresponding maleamic acid which was in turn cyclized in the presence of acetic anhydride and sodium acetate. A thorough structural assessment was carried out to prove the success of this procedure. FM is highly sensitive to ring-opening hydrolysis by atmospheric moisture and must be kept in a dry medium. This investigation was aimed at using FM as an AB-type monomer in a polycondensation based on the Diels-Alder reaction. Preliminary experiments are reported on this novel system which provided the first polycondensates of this kind.