Abstract:

In 2006, Kas'yan et al. reported the synthesis of several bicycle [2.2.1] hept-5-ene-endo, endo-2, 3- dicarboxilic anhydride (endic anhydride) with cyclic non-aromatic amines. It is known that these compounds were used as components of repellent compositions and as agents endowed with sedative activity. One of the products formed was N-(1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-4 pyrazolyl) bicyclo [2.2.1] hept-5-ene-endo, endo-2,3-dicarboximide To prepare the compound 1 is required two steps: a) formation of a derivative norbornene acid and b) closure of imidic ring (Scheme 1) using several days with yields of 86% and 74%, respectively. In view of the synthetic and biological relevance, we proposed the synthesis of the compound (1) in 90 min. (Scheme 2), using three steps: a) synthesis of maleamic acid (4) derived from 4-aminoantypirine (3), b) synthesis of maleimide derived from compound (4) and c) 4+2 coupling reaction (Diels-Alder) using cyclopentadiene.