Chinese Journal of Organic Chemistry >
Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers
Received date: 2022-10-24
Revised date: 2022-11-28
Online published: 2022-12-21
Supported by
National Natural Science Foundation of China(22075144); Natural Science Foundation of Jiangsu Province(BK20200459)
The multi-step synthesis of rigid and multifunctionalized azaadamantane skeletons from small molecules has always been a challenge in the field of adamantane chemistry. In this work, the bisepoxidized intermediate was obtained via ketalization, bromination, elimination, and Prilezhaev oxidation using bicyclo[3.3.1]nonane-2,6-dione as the raw material, which was then ammonolyzed and cyclized to generate 9,10-dihydroxy-2-azaadamantane-4,8-dione bis(ethylene ketal) with ammonia at 120 ℃. After that, 9,10-dinitroyloxy-2-nitro-2-azaadamantane-4,8-dione bis(ethylene ketal) was synthesized by N,O-nitration with the overall yield of 10% over six steps. Furthermore, when the bisepoxidized intermediate was ammonolyzed at 135 ℃, a skeleton isomer 4,10-dihydroxy-2-azaprotoadamantane-5,9-dione bis(ethylene ketal) was formed, which was then transformed to the corresponding O-nitrated and N,O-dinitrated derivatives through N-acetylation, deketalization and nitration, respectively. These provide a reliable method for the subsequent derivation of multifunctional 2-azaadamantane and its skeleton isomer 2-azaprotoadamantane, which might be used as basic scaffolds for high energy density cage-like compounds.
Rongbin Cai , Bing Li , Qi Zhou , Longyi Zhu , Jun Luo . Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2217 -2225 . DOI: 10.6023/cjoc202210027
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