Investigation of the Reactivity of 1-Azido-3-iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions,The Journal of Organic Chemistry

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Investigation of the Reactivity of 1-Azido-3-iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-12-07 , DOI: 10.1021/acs.joc.0c02432
Elisabeth Sitte ₁ , Brendan Twamley ₂ , Nitika Grover ₁ , Mathias O. Senge ₁

Affiliation

The bicyclo[1.1.1]pentane (BCP) unit is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by “click” reactions and integrated cycloaddition–Sonogashira coupling reactions. Thereby, we accessed 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles, and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles on either a modular or a one-pot basis. These methodologies were further utilized for appending porphyrin moieties onto the BCP core.

中文翻译：

“点击”反应条件下1-叠氮基-3-碘代双环[1.1.1]戊烷的反应性研究

双环[1.1.1]戊烷（BCP）单元作为药物分子中的生物等排物正在接受审查。我们通过“点击”反应和集成的环加成－Sonogashira偶联反应，采用一种方法从一种前体1-叠氮基-3-碘代双环[1.1.1]戊烷合成不同的BCP三唑结构单元。因此，我们获得了1,4-二取代三唑，5-碘-1,4,5-三取代三唑和5-炔基化1,4,5-三取代三唑。这为在模块或一锅法基础上合成多取代的BCP三唑提供了条件。这些方法被进一步用于将卟啉部分附加到BCP核心上。

更新日期：2021-01-01

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