在外部无光催化剂条件下，用可见光促进[3 + 2]环加成法合成螺吲哚类化合物

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2024-10-20 DOI:10.1016/j.molstruc.2024.140434

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引用次数: 0

摘要

我们开发了一种可见光促进的 3-烯基吲哚-2-酮与 2-巯基咪唑的[3 + 2]环加成反应，用于构建多种咪唑并[2,1-b]噻唑融合 3,3′-螺氧吲哚。机理研究表明，这种转化是通过可见光激发 3-烯基吲哚-2-酮启动的，而不是电子供体-受体（EDA）复合物促进的过程。总之，我们成功开发了一种在可见光条件下同时构建 C-N 和 C-S 键的方法，并合成了 40 多种具有潜在生物活性的新型含氮和含硫融合杂环化合物，收率高达 99%。该方法操作简单、反应条件温和、原子经济性高、官能团耐受性好，且无需使用任何过渡金属和外部光催化剂。克级反应进一步证明了这一方案的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Visible-light-promoted [3 + 2] cycloaddition for the synthesis of spirooxindoles under external photocatalyst-free conditions

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Visible-light-promoted [3 + 2] cycloaddition for the synthesis of spirooxindoles under external photocatalyst-free conditions

A visible-light-promoted [3 + 2] cycloaddition of 3-alkenylindole-2-ones with 2-mercaptoimidazoles for the construction of diverse imidazo[2,1-b]thiazole fused 3,3′-spirooxindoles has been developed. Mechanism studies have shown that this transformation is initiated through visible-light excitation of 3-alkenylindole-2-ones, rather than an electron donor-acceptor (EDA) complexes-promoted process. In summary, we have successfully developed a method for simultaneously constructing C−N and C−S bonds under visible-light conditions, and synthesized over 40 examples of new nitrogen- and sulfur-containing fused heterocyclic compounds with potential biological activity with a yield of up to 99 %. This method exhibits simple operation, mild reaction conditions, high atom economy, good functional group tolerance and does not require the use of any transition metals and external photocatalysts. Gram-scale reaction further demonstrates the practicality of this protocol.

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.