Azapropellanes are of great interest in many disciplines, including materials science and medicinal chemistry. Various synthetic approaches for azapropellanes have been explored; however, the synthetic study of the polyazapropellane skeleton containing five or more nitrogen atoms is rare. Here, we report a simple yet highly efficient protocol for the synthesis of the hexaaza[3.3.3]propellane skeleton as a building block for high energy materials for the first time. The key reactions include the Boc₂O-assisted cyclization of glycoluril diamine without a column purification step and the first full reduction of all the three carbonyl groups to the methylene groups through a combination of LiAlH₄ and DIBAL-H. All the structures were confirmed by spectroscopic and X-ray analyses.

氮杂螺菌素在包括材料科学和药物化学在内的许多学科中都引起了极大的兴趣。已经探索了各种合成的氮杂丙二酮方法。但是，对含五个或更多氮原子的聚氮杂丙炔骨架的合成研究很少。在这里，我们首次报告了一种简单但高效的协议，用于合成六氮杂[3.3.3]丙炔骨架，以此作为高能材料的基础。关键反应包括无需柱纯化步骤的Boc ₂ O辅助的甘脲二胺环化，以及通过LiAlH ₄和DIBAL-H的结合将所有三个羰基首次完全还原为亚甲基。所有结构通过光谱和X射线分析确认。