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

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 r...

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Bibliographic Details
Published in:Tetrahedron 2018-01, Vol.74 (1), p.130-134
Main Authors: Lee, Byeongil, Shin, Moonyong, Seo, Youngran, Kim, Myeong Hak, Lee, Hye Ryoung, Kim, Jin Seok, Chung, Kyu-hyun, Yoo, Dongwon, Kim, Young Gyu
Format: Article
Language:English
Subjects:
Azapropellane
Cyclization
Propellane
Urea reduction
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.11.046