Synthesis of 2,4,6,8,9,11-hexaaza[3.3.3]propellanes as a new molecular skeleton for explosives

초록

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 Boc(2)O-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 LiAIH4 and DIBAL-H. All the structures were confirmed by spectroscopic and X-ray analyses. (C) 2017 Elsevier Ltd. All rights reserved.

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