Synthesis of blue light emitting heterocyclesviacyclization of 2-pyridine derived 4-azido-r1,2,3-triazoles

An efficient synthesis of 2-pyridine derived 4-azido-1,2,3-triazoles was elaborated using the corresponding dichlorodiazadienes as precursors. The reaction of the prepared 2-azine substituted diazadienes with sodium azide permits the preparation of target triazoles isolated in up to 92% yield. Subsequent thermal cyclization was studied. Elimination of molecular nitrogen promoted the cyclization of nitrene at the azine nitrogen. As a result, a family of 2H-[1,2,3]triazolo[4′,5′:3,4]pyrazolo[1,5-a]pyridin-5-ium-4-ides was prepared. The synthesized compounds are members of a new heterocyclic system. Moreover, these compounds are new attractive blue light emitting molecules. © The Royal Society of Chemistry 2021.