Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives,Chemical Science

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Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives
Chemical Science ( IF 7.6 ) Pub Date : 2022-08-15 , DOI: 10.1039/d2sc03166c
Xi-Shang Sun ₁ , Xin-Yu Diao ₁ , Xiu-Qin Dong ₁ , Chun-Jiang Wang _{1,

2}

Affiliation

A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N-2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.

中文翻译：

碱基促进的级联β-F-消除/电环化/Diels-Alder/retro-Diels-Alder 反应：高效获得 δ-咔啉衍生物

通过碱促进的级联β-F-消除/电环化/Diels-Alder / retro-Diels-Alder 反应，开发了一种偶然且高效的方法来构建各种 δ-咔啉衍生物。-2,2,2-三氟乙基靛蓝酮亚胺酯与炔烃的产率从良好到高产率，具有出色的区域/化学选择性控制。此外，根据制备的反应中间体和对照实验结果，提出了合理的反应途径。通过简单的合成转化，δ-咔啉产物可以很容易地转化为新的手性 Py-box 型配体。这一突出策略具有无金属条件、优异的区域/化学选择性、良好至高产率和出色的底物耐受性等优点。重要的是，这些迷人的 δ-咔啉衍生物产品的潜在应用在铁离子的识别中得到了很好的证明。

更新日期：2022-08-15

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