Molecular Editing of 5-Alkynyl-1,2,3-triazines via a Silver-Mediated Skeletal Remodeling Approach: Solvent-Controlled Switchable Synthesis of Functionalized Pyrroles and Furans.

We present a skeletal remodeling approach using 5-alkynyl-1,2,3-triazines (3) for the switchable construction of functionalized pyrroles (4) and furans (5). This flexible and adaptable method for heterocycle editing involves the nucleophilic ring opening of 1,2,3-triazines, followed by subsequent cyclization. The process can be finely tuned by adjusting the silver-mediated conditions and solvent systems. This protocol provides a new avenue for the efficient synthesis of five-membered aromatic heterocycles.