Novel and selective synthesis of unsymmetrical azine derivatives via a mild reaction

A new, convenient, benign procedure for the one-step synthesis of unsymmetrical azines by reaction of aromatic aldehyde derivatives and hydrazine sulfate in triethylamine and absolute ethanol solution is presented. This methodology is more useful than the well-known two-step variant (involving preparation of a hydrazone and subsequent reaction with an aldehyde), because it enables the formation of unsymmetrical azines in a one-pot and rapid method without formation of any by-product or without requirement to separate the hydrazone intermediate. The mildness, selectivity, short reaction time, easy work-up, and applicability for large-scale reactions are the main advantages of this protocol for the synthesis of unsymmetrical azine derivatives. Structures of all new compounds were elucidated by H-1 and C-13 NMR, IR, MS, and CHN measurements.