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Safety is fundamental for the practical development and application of energetic materials. Three tricyclic energetic compounds, namely, 1,3-di(1H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine (ATDT), 5′-nitro-3-(1H-tetrazol-5-yl)-2′H-[1,3′-bi(1,2,4-triazol)]-5-amine (ATNT), and 1-(3,4-dinitro-1H-pyrazol-5-yl)-3-(1H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine (ATDNP), were effectively synthesized through a simple two-step synthetic route. The introduction of intramolecular hydrogen bonds resulted in excellent molecular planarity for the three new compounds. Additionally, they exhibit regular crystal packing, leading to numerous intermolecular hydrogen bonds and π–π interactions. Benefiting from planar tricyclic structural features, ATDT, ATNT, and ATDNP are insensitive (IS > 60 J, FS = 360 N) when exposed to external stimuli. Furthermore, ATNT (Td = 361.1 °C) and ATDNP (Td = 317.0 °C) exhibit high decomposition temperatures and satisfying detonation performance. The intermolecular hydrogen bonding that produced this planar tricyclic molecular structure serves as a model for the creation of innovative multiple heterocycle energetic materials with excellent stability. [ABSTRACT FROM AUTHOR]

A novel and green route have been developed for the electrochemical synthesis of 3-halogenated spiro[4.5]trienones based on dearomative spirocyclization of alkynes with NaX (Br, I) as the halogen source. This transformation was performed in an undivided cell under mild conditions. A wide range of substituted 3-halogenated spiro[4.5]trienones products was prepared in moderate-to-good yields, showing a broad scope and functional group tolerance. In addition, this approach was further extended to access fused tricyclic 6,7-dihydro-3H-pyrrolo[2,1-j]quinoline-3,9(5H)-diones.