A Molecular Cage Accessed by Threefold Click Reaction of a C3v-Symmetric Triazido-Functionalized Tribenzotriquinacene,The Journal of Organic Chemistry

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A Molecular Cage Accessed by Threefold Click Reaction of a C3v-Symmetric Triazido-Functionalized Tribenzotriquinacene
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-01-25 , DOI: 10.1021/acs.joc.3c01349
Shuai-Nan Liu ₁ , Qing-Xia Ren ₁ , Yun-Tao Ding ₁ , Xiao-Ping Cao ₁ , Zi-Fa Shi ₁ , Hak-Fun Chow ₂ , Dietmar Kuck ₃

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The hitherto unknown hexakis(halomethyl)-functionalized tribenzotriquinacenes (TBTQs) 9 and 10 were synthesized from the key 4b,8b,12b-tribromo-TBTQ derivative 6 by an improved route in 67% overall yield. Extension of the bowl-shaped framework of 9 or 10 by threefold condensation with propargylamine or 2-azidoethylamine afforded the corresponding TBTQ-trialkyne 11 and TBTQ-triazide 12, respectively. While attempts to construct bis-TBTQ cages, including homodimerization of 11 and heterocoupling of 11 with 12, were unsuccessful, triazide 12 was found to undergo threefold [3 + 2]-cycloaddition with 3-ethynylaniline and phloroglucinol tripropargyl ether under click chemistry conditions. The latter reaction enabled facile capping of the TBTQ bowl to give the novel cage compound 5 in 22% yield.

中文翻译：

通过 C3v 对称三叠氮基官能化三苯并三醌的三重点击反应进入分子笼

由关键的4b,8b,12b-三溴-TBTQ衍生物6通过改进的路线合成了迄今为止未知的六（卤甲基）官能化三苯并三醌（TBTQ） 9和10 ，总产率为67%。 9或10的碗状骨架通过与炔丙胺或2-叠氮乙胺三倍缩合而延伸，分别得到相应的TBTQ-三炔11和TBTQ-三叠氮化物12 。虽然构建双-TBTQ笼的尝试，包括11的同二聚化和11与12的杂偶联均未成功，但发现三叠氮12在点击化学条件下与3-乙炔基苯胺和间苯三酚三炔丙基醚发生三重[3+2]-环加成。后一个反应能够轻松封盖 TBTQ 碗，以 22% 的产率得到新型笼状化合物5 。

更新日期：2024-01-25

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