A Convenient Way to Methylated 2-Imidazolines. Syntheses of Fluorene and Triazine Cyclic Diamidines

Summary. One N-methyl- and 4-substituted 2-imidazolines are described. Fluorene bisimidazolines were obtained in good yield (64–92%), starting from 2,7-dicyanofluorene and ammonium sulfide. In a two-step procedure the crude bisthioamide was reacted with excess diaminoalkane-ethanol (1:1 mixture) in an oil bath. This new procedure is superior over standard methods. For the sake of comparison, a new triazine bisimidazoline was prepared by direct conversion of the appropriate bisnitrile. Preliminary in vitro studies have shown an interesting anticancer activity of this compound (NSC 710607) against diverse human cancer types, including colon, CNS, melanoma, breast, non-small cell lung, and ovarian.