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可见光诱导的自由基级联磺酰化/环化反应合成吲哚并吡啶衍生物

Visible-light-induced radical cascade sulfonylation/cyclization towards indole-fused pyridine derivatives.

作者信息

Du Qin, Pan Ruohan, Chen Yu, Tang Yucai

机构信息

Changde Hospital, Xiangya School of Medicine, Central South University (The First People's Hospital of Changde City) Changde 415000 China

College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Engineering Technology Research Center of Key Preparation Technology of Biomedical Polymer Materials Changde 415000 China.

出版信息

RSC Adv. 2025 Jan 2;15(1):216-222. doi: 10.1039/d4ra08000a.

DOI:10.1039/d4ra08000a
PMID:39758899
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11694507/
Abstract

Indole-fused pyridines are an important motif in pharmaceuticals and functional molecules. A visible-light induced Ru(bpy)Cl·6HO catalyzed radical cascade sulfonylation/cyclization strategy for the synthesis of indole-fused pyridine derivatives was developed. Diverse indole-fused pyridines bearing different functional groups were obtained in moderate to good yields. Compared with previous work, the easily accessible starting materials, molecular nitrogen as byproduct, and eco-friendly visible light as an energy source all make this transformation more sustainable and practical.

摘要

吲哚并吡啶是药物和功能分子中的重要结构单元。开发了一种可见光诱导的Ru(bpy)Cl·6H₂O催化的自由基串联磺酰化/环化策略,用于合成吲哚并吡啶衍生物。以中等至良好的产率获得了带有不同官能团的多种吲哚并吡啶。与先前的工作相比,起始原料易于获得、副产物为分子氮以及使用环保的可见光作为能源,所有这些都使这种转化更具可持续性和实用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/3eff1c95cbb5/d4ra08000a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/bd098edbc07b/d4ra08000a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/9a7c7a99b768/d4ra08000a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/6f432187dbbe/d4ra08000a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/3eff1c95cbb5/d4ra08000a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/bd098edbc07b/d4ra08000a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/9a7c7a99b768/d4ra08000a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/6f432187dbbe/d4ra08000a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a691/11694507/3eff1c95cbb5/d4ra08000a-s3.jpg

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本文引用的文献

1
Photoredox Catalyzed Radical Cascade Aroylation (Sulfonylation)/Cyclization Enables Access to Fused Indolo-pyridones.
J Org Chem. 2021 Dec 17;86(24):18042-18055. doi: 10.1021/acs.joc.1c02335. Epub 2021 Dec 6.
2
Synthesis of indolo[2,1-]isoquinoline derivatives metal-free radical cascade cyclization.吲哚并[2,1-]异喹啉衍生物的无金属自由基级联环化合成。
Org Biomol Chem. 2021 Dec 8;19(47):10376-10384. doi: 10.1039/d1ob01917a.
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Aerobic Oxidative Cascade Thiolation and Cyclization to Construct Indole-Fused Isoquinolin-6(5)-one Derivatives in EtOH.乙醇中构建吲哚并异喹啉-6(5)-酮衍生物的有氧氧化级联硫代和环化反应
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Photocatalysis in the Life Science Industry.生命科学产业中的光催化
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Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-]isoquinolin-6(5)-ones and indolin-2-ones.铁催化自由基环化反应合成锗取代的吲哚并[2,1-]异喹啉-6(5)-酮和吲哚啉-2-酮。
Chem Commun (Camb). 2021 Sep 14;57(73):9276-9279. doi: 10.1039/d1cc03907e.
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Visible-Light-Induced C(sp)-C(sp) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins.可见光诱导 C(sp)-C(sp) 偶联反应用于 3-官能化香豆素的区域选择性合成。
J Org Chem. 2021 Jul 16;86(14):9552-9562. doi: 10.1021/acs.joc.1c00848. Epub 2021 Jun 30.
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