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钌催化的位点选择性C-H活化:通往C5-取代氮杂黄烷酮的途径。

Ruthenium-catalyzed, site-selective C-H activation: access to C5-substituted azaflavanone.

作者信息

Bakthadoss Manickam, Reddy Tadiparthi Thirupathi, Sharada Duddu S

机构信息

Department of Chemistry, Pondicherry University Puducherry - 605014 India

Department of Chemistry, Indian Institute of Technology Hyderabad Telangana-502285 India.

出版信息

RSC Adv. 2020 Aug 26;10(52):31570-31574. doi: 10.1039/d0ra06580c. eCollection 2020 Aug 21.

DOI:10.1039/d0ra06580c
PMID:35520642
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9056431/
Abstract

A site-selective ruthenium-catalyzed keto group assisted C-H bond activation of 2-aryl tetrahydroquinoline (azaflavanone) derivatives has been achieved with a variety of alkenes for the first time. A wide range of substrates was utilized for the synthesis of a wide variety of alkenylated azaflavanones. This simple and efficient protocol provides the C5-substituted azaflavanone derivatives in high yields with a broad range of functional group tolerance. Further, the C5-alkenylated products were converted into substituted 2-aryl quinoline derivatives in good yields.

摘要

首次实现了钌催化的2-芳基四氢喹啉(氮杂黄烷酮)衍生物的酮基辅助C-H键与多种烯烃的位点选择性活化。多种底物被用于合成多种烯基化氮杂黄烷酮。这种简单有效的方法以高收率提供了具有广泛官能团耐受性的C5-取代氮杂黄烷酮衍生物。此外,C5-烯基化产物以良好的收率转化为取代的2-芳基喹啉衍生物。

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3
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RSC Adv. 2024 Apr 23;14(19):13306-13310. doi: 10.1039/d4ra01289e. eCollection 2024 Apr 22.
4
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Chem Sci. 2023 Feb 23;14(22):5880-5886. doi: 10.1039/d2sc06206b. eCollection 2023 Jun 7.
钯催化的氧杂苯并恶嗪衍生物的化学选择性和位点选择性 C-H 乙酰化和羟化反应。
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4
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6
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