Electrosynthesis of 1,2,3-Benzotriazines through an Iodide-Catalyzed Skeletal Editing of 3-Aminoindazoles

Abstract

This report describes an environmentally benign synthesis of 1,2,3-benzotriazines through an iodide-catalyzed electro-oxidative N-centered [1,2]-rearrangement of 3-aminoindazoles. The developed method demonstrates the activation of heteroatoms via electrochemically generated reactive iodide species without using any metal catalysts and peroxides. The protocol features practical and mild reaction conditions and displays a wide substrate scope. Various mechanistic experiments and cyclic voltammetric studies have been instrumental in elucidating the reaction mechanism, operating via a skeletal rearrangement of 3-aminoindazoles.

Keywords: Electrochemistry; Green synthesis; Iodide-catalysis; Molecular editing; Redox.