Synthesis of Nitro-Functionalized Polynitrogen Tricycles Bearing a Central 1,2,3-Triazolium Ylide.

This paper describes the synthesis of unprecedented fused nitroazaheterocyclic ring systems. Nitro tricycles with a central 1,2,3-triazole ring were obtained via a nitrene-mediated reaction of azidonitrobis(hetaryl) derivatives under thermolysis. The cyclization proceeded with complete chemoselectivity for the desired N-N bond formation. The key azidonitro bicycles were synthesized through an aromatic nucleophilic substitution from nitroazoles and 3-azido-2-chloropyrazine. [ABSTRACT FROM AUTHOR]