Background: The chemistry of tetrazine has gained an increased attention in the last decades due to
their applications materials science and coordination chemistry. 1,3-Dipolar cycloaddition of nitrile imines to C60
is the standard method for annelating the pyrazoline ring to the fullerene sphere. The interest in the chemistry of
hydrazonoyl halides is a consequence of the fact that they undergo a wide variety of reactions, which provide
routes heterocyclic compounds.
Results: A facile synthesis of polytetrazines based on bishydrazonoyl halides is described. Bis(pyrazolino
fullerenes) were synthesized from the reaction of bishydrazonoyl halides with fullerene. Moreover, an efficient
synthesis of new polypyrazoline-maleimide is reported. The synthetic methods involves 1,3-dipolar cycloaddition
reactions of bisnitrilimines (generated in situ by the effect of the triethylamine on bishydrazonoyl halides)
to give the final products. Structures of the newly synthesized products were elucidated via elemental analyses
and spectral data (FT-IR, MS, 1H and 13C NMR).
Conclusion: Novel heterocycles of polytetrazines, bis(pyrazolinofullerenes) and Polypyrazoline-maleimide
based on 1,3-dipolar cycloaddition reaction are reported.