Intramolecular Carbonylative C–H Functionalization of 1,2,3‐ Triazoles for the Synthesis of Triazolo[1,5‐a]indolones,Advanced Synthesis & Catalysis

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Intramolecular Carbonylative C–H Functionalization of 1,2,3‐ Triazoles for the Synthesis of Triazolo[1,5‐a]indolones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-02-21 , DOI: 10.1002/adsc.201601388
Cedrick Veryser ₁ , Gert Steurs ₁ , Luc Van Meervelt ₂ , Wim M. De Borggraeve ₁

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This study presents a synthesis of 4H‐[1,2,3]triazolo[1,5‐a]indol‐4‐ones. The key step in the synthesis of this new heterocyclic scaffold is an intramolecular cyclization via an unprecedented carbonylative C–H functionalization of 1‐(2‐bromoaryl)‐1,2,3‐triazoles. Isotopic labelling of the carbonyl carbon atom is possible using near stoichiometric amounts of ¹³CO. Additionally, an alternative pathway via carbonylative Sonogashira coupling followed by a two‐step, one‐pot azidation/cycloaddition is also investigated, giving rise to the same scaffold.

中文翻译：

1,2,3-三唑的分子内羰基化CH官能团用于合成三唑并[1,5-a]吲哚酮

这项研究提出了4 H- [1,2,3]三唑[1,5 - a ]吲哚-4-酮的合成。合成这种新型杂环骨架的关键步骤是通过空前的1-（2-溴芳基）-1,2,3-三唑的羰基化CH功能将分子内环化。可以使用接近化学计量的¹³ CO进行羰基碳原子的同位素标记。此外，还研究了通过羰基Sonogashira偶联然后进行两步单罐叠氮化/环加成反应的替代途径，从而产生了相同的骨架。

更新日期：2017-02-21

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