Reaction of C-aroyl-N-aryl nitrilimines with selected aliphatic keto-hydrazones and keto-methylhydrazones

Abstract

C-Benzoyl-and C-2-naphthoyl nitrilimines (2) react with methylhydrazones of aliphatic ketones (3, R1= CH3) to afford the cyclocondensation products 1, 2, 4, 5-tetrazines (4, 5). The reaction of simple hydrazones (3, R1= H) with the same nitrilimines gives the acyclic electrophilic addition products (6, 7), rather than the cyclocondensation tetrazine products.