Heterocyclic Nitrilimines and Their Use in the Synthesis of Complex High-Nitrogen Materials

We show the ability of a nitrilimine prepared from 3-amino-5-nitro-1,2,4-triazole to undergo various cyclization and rearrangement reactions, giving a beautiful diversity of nitrogen-rich heterocyclic products. This chemistry includes the first cyclization of a nitrilimine with a diazonium species, giving a tetrazole, a previously unknown transformation, as well as leading to the creation of several new energetic materials with backbones not available by traditional techniques. New materials prepared were characterized both chemically (multinuclear NMR, IR, mass spectrometry, and elemental analysis) and energetically, with sensitivities and performances reported.

Automated summary

The study showcases the diverse nitrogen-rich heterocyclic products prepared from a nitrilimine, with the first cyclization of a nitrilimine with a diazonium species resulting in the formation of a tetrazole, a previously unknown transformation. Characterization of the new materials was done both chemically and energetically, with sensitivities and performances reported.