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.