Design and Synthesis of Cage Molecules as High Energy Density Materials for Aerospace Applications,ChemCatChem

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Design and Synthesis of Cage Molecules as High Energy Density Materials for Aerospace Applications
ChemCatChem ( IF 3.8 ) Pub Date : 2020-11-06 , DOI: 10.1002/cctc.202001475
Sambasivarao Kotha ₁ , Subba Rao Cheekatla ₁ , Milind Meshram ₂

Affiliation

This account deals with our work on cage systems that was reported during the past two decades. Here, we summarized various new synthetic routes to diverse cage polycycles by employing Claisen rearrangement, Diels−Alder (DA) reaction, [2+2] photocycloaddition, Grignard addition, Fischer indolization, ring‐closing metathesis (RCM), Van Leusen oxazole synthesis, and rearrangement reaction as key steps. Several heterocyclic cage frameworks (oxacycles and oxazoles), polycyclic bisindoles, cage spirocycles, cage energetic systems, D₃‐trishomocubanes, cage propellanes and unusual polycycles were designed starting with inexpensive and easily accessible starting materials. In some occasions, we also prepared biologically important triquinane frameworks starting with readily available cage diones via photo‐thermal olefin metathesis strategy under microwave irradiation conditions. This new protocol avoids specialized equipment such as flash vacuum pyrolysis. Additionally, we have also shown interesting rearrangements in cage frameworks to generate unusual new and cage systems with the aid of the Lewis acids such as BF₃.OEt₂. Moreover, these functionalized cage systems can be considered as a useful candidates in material science, medicinal chemistry, and also in drug in design.

中文翻译：

笼型分子作为航空航天应用高能密度材料的设计与合成

该帐户处理了我们过去二十年来在笼式系统方面的工作。在这里，我们总结了通过使用克莱森重排，狄尔斯-阿尔德（DA）反应，[2 + 2]光环加成，格利雅（Grignard）加成，菲舍尔吲哚化，闭环复分解（RCM），范鲁森（Van Leusen oxazole）合成等各种途径合成多种笼型多环化合物的新途径，并将重排反应作为关键步骤。几个杂环笼骨架（草环和恶唑），多环双吲哚，笼螺环，笼能量系统，D ₃Trishomocubanes，笼式螺旋桨和不寻常的多环化合物的设计始于廉价且易于获得的原料。在某些情况下，我们还通过微波辐射条件下的光热烯烃复分解策略，从易于获得的笼二酮开始，准备了具有重要生物学意义的三喹烷骨架。该新协议避免了诸如闪蒸真空热解的专用设备。此外，我们还显示了在笼状结构中有趣的重排，借助路易斯酸（例如BF ₃ .OEt _2）生成不寻常的新笼状系统。而且，这些功能化的笼式系统可以被认为是材料科学，药物化学以及药物设计中的有用候选物。

更新日期：2020-12-16

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