• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

通过 1,2-二氢吡啶与 Selectfluor 的亲电氟化反应合成氟化 3,6-二氢吡啶和 2-(氟甲基)吡啶。

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor.

机构信息

Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, Latvia.

Institute of Organic Chemistry NAS of Ukraine, Murmanska Str. 5, 02660 Kyiv, Ukraine.

出版信息

Molecules. 2020 Jul 9;25(14):3143. doi: 10.3390/molecules25143143.

DOI:10.3390/molecules25143143
PMID:32660085
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7397266/
Abstract

New fluorinated 3,6-dihydropyridines were obtained by the electrophilic fluorination of 1,2-dihydropyridines with Selectfluor. These 3-fluoro-3,6-dihydropyridines were easily converted to corresponding pyridines by the elimination of hydrogen fluoride under mild conditions. A new approach to the synthesis of methyl 2-(fluoromethyl)-5-nitro-6-arylnicotinates by the fluorination of 3-fluoro-2-methyl-5-nitro-3,6-dihydropyridines or 1,2-dihydropyridines with Selectfluor has been developed.

摘要

新的氟化 3,6-二氢吡啶通过 1,2-二氢吡啶的 Selectfluor 亲电氟化得到。这些 3-氟-3,6-二氢吡啶在温和条件下通过消除氟化氢很容易转化为相应的吡啶。通过 Selectfluor 对 3-氟-2-甲基-5-硝基-3,6-二氢吡啶或 1,2-二氢吡啶进行氟化,开发了一种合成甲基 2-(氟甲基)-5-硝基-6-芳基烟酸酯的新方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/552803d59b7c/molecules-25-03143-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/cb1f2bf39b0a/molecules-25-03143-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/74bb4750cbbd/molecules-25-03143-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/be1da9bb5d64/molecules-25-03143-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/552803d59b7c/molecules-25-03143-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/cb1f2bf39b0a/molecules-25-03143-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/74bb4750cbbd/molecules-25-03143-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/be1da9bb5d64/molecules-25-03143-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d68/7397266/552803d59b7c/molecules-25-03143-sch002.jpg

相似文献

1
Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor.通过 1,2-二氢吡啶与 Selectfluor 的亲电氟化反应合成氟化 3,6-二氢吡啶和 2-(氟甲基)吡啶。
Molecules. 2020 Jul 9;25(14):3143. doi: 10.3390/molecules25143143.
2
Stereoselective synthesis of conjugated fluoro enynes.手性氟烯炔的立体选择性合成。
J Org Chem. 2012 Oct 5;77(19):8417-27. doi: 10.1021/jo300971w. Epub 2012 Sep 24.
3
Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp(3))-H Bonds.钯催化的未活化 C(sp(3))-H 键的位点选择性氟化反应。
Org Lett. 2015 Aug 7;17(15):3738-41. doi: 10.1021/acs.orglett.5b01710. Epub 2015 Jul 24.
4
Fluorination methods in drug discovery.药物研发中的氟化方法。
Org Biomol Chem. 2016 Sep 28;14(36):8398-427. doi: 10.1039/c6ob00764c. Epub 2016 Aug 10.
5
Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.用于三氟甲基和二氟甲基芳烃合成的催化脱羧氟化反应。
Org Lett. 2013 Jun 7;15(11):2648-51. doi: 10.1021/ol4009377. Epub 2013 May 20.
6
Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde.(2R)-和(2S)-氟代他汀的非对映选择性合成及构象分析:一种基于手性醛的有机催化氟化方法
Org Lett. 2016 Feb 19;18(4):662-5. doi: 10.1021/acs.orglett.5b03592. Epub 2016 Feb 10.
7
Recent progress in asymmetric fluorination and trifluoromethylation reactions.近年来不对称氟化和三氟甲基化反应的研究进展。
Curr Top Med Chem. 2014;14(7):901-40. doi: 10.2174/1568026614666140202205531.
8
Selective C-H fluorination of pyridines and diazines inspired by a classic amination reaction.受经典胺化反应启发的吡啶和哒嗪的选择性 C-H 氟化。
Science. 2013 Nov 22;342(6161):956-60. doi: 10.1126/science.1243759.
9
Tandem asymmetric Michael reaction-intramolecular Michael addition. An easy entry to chiral fluorinated 1,4-dihydropyridines.串联不对称迈克尔反应-分子内迈克尔加成。手性氟化 1,4-二氢吡啶的简单入口。
Org Lett. 2010 Aug 6;12(15):3484-7. doi: 10.1021/ol101318t.
10
Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.Using HF as a Source of Fluorine in Kitamura's Electrophilic Fluorination.
Molecules. 2020 Apr 30;25(9):2116. doi: 10.3390/molecules25092116.

本文引用的文献

1
-Fluorobenzenesulfonimide: a useful and versatile reagent for the direct fluorination and amination of (hetero)aromatic C-H bonds.氟苯磺酰亚胺:一种用于(杂)芳族C-H键直接氟化和胺化的有用且通用的试剂。
RSC Adv. 2020 Apr 29;10(28):16756-16768. doi: 10.1039/d0ra00324g. eCollection 2020 Apr 23.
2
Transition-Metal-Free Addition Reaction for the Synthesis of 3-(Aminobenzylidene/aminoalkylidene)indolin-2-ones and Its Synthetic Applications.无过渡金属参与的加成反应在 3-(氨亚苄基/亚氨基烷基)吲哚啉-2-酮的合成及其合成应用中的研究。
J Org Chem. 2019 Nov 1;84(21):13516-13527. doi: 10.1021/acs.joc.9b01771. Epub 2019 Oct 10.
3
Solvent Effects: Syntheses of 3,3-Difluorooxindoles and 3-Fluorooxindoles from Hydrazonoindolin-2-one by Selectfluor.
溶剂效应:通过Selectfluor由肼基吲哚啉-2-酮合成3,3-二氟氧化吲哚和3-氟氧化吲哚
J Org Chem. 2018 Jun 15;83(12):6762-6768. doi: 10.1021/acs.joc.8b00737. Epub 2018 May 24.
4
Conformational Preference of 2-(Halomethyl)- and 2-(Oxymethyl)Pyridines: Microwave Spectrum, Ab Initio, and MM3 Studies of 2-(Fluoromethyl)Pyridine.2-(卤甲基)-和2-(氧甲基)吡啶的构象偏好:2-(氟甲基)吡啶的微波光谱、从头算和MM3研究
Chemistry. 1996 May;2(5):516-522. doi: 10.1002/chem.19960020510.
5
Decarboxylative Fluorination of Electron-Rich Heteroaromatic Carboxylic Acids with Selectfluor.用 Selectfluor 对富电子杂环芳香族羧酸进行脱羧氟化反应。
Org Lett. 2017 Mar 17;19(6):1410-1413. doi: 10.1021/acs.orglett.7b00335. Epub 2017 Mar 3.
6
Structure based medicinal chemistry approach to develop 4-methyl-7-deazaadenine carbocyclic nucleosides as anti-HCV agent.基于结构的药物化学方法开发 4-甲基-7-脱氮嘌呤碳环核苷作为抗 HCV 药物。
Bioorg Med Chem Lett. 2012 Dec 15;22(24):7742-7. doi: 10.1016/j.bmcl.2012.09.072. Epub 2012 Oct 13.
7
Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).高对映选择性氟化未保护的 3-取代氧吲哚:BMS 204352(MaxiPost)的一步合成。
J Org Chem. 2012 Oct 19;77(20):9148-55. doi: 10.1021/jo301705t. Epub 2012 Oct 10.
8
Silver-mediated fluorination of aryl silanes.芳基硅烷的银介导氟化反应。
Tetrahedron. 2011 Jun 17;67(24):4449-4454. doi: 10.1016/j.tet.2011.02.077.
9
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu.针对 H-Pu 94 个元素,进行了一致且准确的从头计算(ab initio)密度泛函色散校正(DFT-D)参数化。
J Chem Phys. 2010 Apr 21;132(15):154104. doi: 10.1063/1.3382344.
10
Measurement of long-range 1H-19F scalar coupling constants and their glycosidic torsion dependence in 5-fluoropyrimidine-substituted RNA.5-氟嘧啶取代RNA中远程¹H-¹⁹F标量耦合常数的测量及其糖苷扭转依赖性
J Am Chem Soc. 2006 May 3;128(17):5851-8. doi: 10.1021/ja060165t.