Base Mediated Sequential Nitrogen Insertion and Benzotriazolation of p-Quinone Methides.

Herein, we report a base-mediated, one-pot protocol for the synthesis of functionalized benzotriazole derivatives via in situ generation of benzotriazoles from benzene-1,2-diamines and tert-butyl nitrite. The transformation proceeds through nitrogen insertion, followed by a subsequent 1,6-aza-Michael addition with p-quinone methides, enabling efficient C-N bond formation. Notably, the developed method operates under mild, transition-metal-free conditions and is performed under an open-air atmosphere, offering a practical and environmentally benign approach to structurally diverse benzotriazoles and demonstrated 34 examples of ≤87% yield with wide functional group tolerance.