A simple evaluation of Lewis acids revealed that Α-hydrazonyl chlorides undergo [2+3] cycloadditions reaction with activated olefins to form the cycloaddition products. The Α-hydrazonyl chlorides in presence of Lewis acids generate nitrile imines in situ which react with dipolarphiles to afford the cycloaddition products. The LiNO3, Cu(NO3)2, Cu(SO)4.5H2O, Ag2CO3, NiNO3, Ce(NO3)2-catalyzed 1,3-dipolar reactions led to the synthesis of respective pyrazoline compounds and the results create new possibilities for exploiting the metal salt-catalyzed cycloaddition reaction and facile synthesis of five membered heterocycles. In addition to these the role of tetrahexylammonium chloride related to a kind micellar catalysis in cycloaddition reactions is also examined.
We thank the National Institutes of Health (G12RR13459) and the National Science Foundation (HRD-0401730) for their generous financial support.