Stereoselective Synthesis of Diaza-Hexatrienes via [1,6]- O -to- N Group Transfer Strategy

Herein, we report a transition metal-free synthesis of Z-configured 2,3-diaza-1,3,5-hexatrienes via a base-mediated rearrangement of O-substituted salicylaldehyde N-tosylhydrazones. This unprecedented O-to-N group transfer occurs under mild conditions, exhibits a broad substrate scope, and tolerates diverse functional groups. The resulting diazatrienes serve as precursors for heterocycles and photoswitches. This rearrangement introduces a new synthetic strategy distinct from classical phenol-based rearrangements.