通过芳基重氮盐与腈的偶联制备取代菲啶：一种无金属方法。
Preparation of substituted phenanthridines from the coupling of aryldiazonium salts with nitriles: a metal free approach.
作者信息
Ramanathan Mani, Liu Shiuh-Tzung
机构信息
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
出版信息
J Org Chem. 2015 May 15;80(10):5329-36. doi: 10.1021/acs.joc.5b00579. Epub 2015 May 7.
PMID:25923346
Abstract
A transition metal free approach for the synthesis of substituted phenanthridines from the coupling reaction of aryldiazonium tetrafluoroborates with nitriles has been developed. This operationally simple protocol proceeds through a substitution of aryldiazonium with nitriles followed by an intramolecular arylation to provide the corresponding phenanthridines in moderate to excellent yields.
摘要
已开发出一种无过渡金属的方法，用于通过芳基四氟硼酸重氮盐与腈的偶联反应合成取代菲啶。该操作简单的方案通过芳基重氮盐与腈的取代反应，然后进行分子内芳基化反应，以中等至优异的产率提供相应的菲啶。
相似文献
1
Preparation of substituted phenanthridines from the coupling of aryldiazonium salts with nitriles: a metal free approach.通过芳基重氮盐与腈的偶联制备取代菲啶：一种无金属方法。
J Org Chem. 2015 May 15;80(10):5329-36. doi: 10.1021/acs.joc.5b00579. Epub 2015 May 7.
2
Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles.通过二芳基碘鎓盐与腈的串联环化反应合成菲啶衍生物。
Org Biomol Chem. 2014 Oct 28;12(40):7904-8. doi: 10.1039/c4ob01504e.
3
A four-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, 1,2-dibromoethane, and hydrazines.芳基四氟硼酸重氮盐、二氧化硫、1,2 - 二溴乙烷和肼的四组分反应。
Org Biomol Chem. 2015 Nov 7;13(41):10370-5. doi: 10.1039/c5ob01765c.
4
Direct arylation of N-heteroarenes with aryldiazonium salts by photoredox catalysis in water.在水中通过光氧化还原催化实现氮杂芳烃与芳基重氮盐的直接芳基化反应。
Chemistry. 2014 Mar 3;20(10):2960-5. doi: 10.1002/chem.201304120. Epub 2014 Feb 5.
5
6-Perfluoroalkylated phenanthridines via radical perfluoroalkylation of isonitriles.通过腈的自由基全氟烷基化反应合成 6-全氟烷基菲啶。
Org Lett. 2014 Aug 1;16(15):3990-3. doi: 10.1021/ol5018195. Epub 2014 Jul 23.
6
Synthesis of polysubstituted phenanthridines via ligand-free copper-catalyzed annulation.无配体铜催化环化合成多取代菲啶。
Org Lett. 2014 Sep 5;16(17):4642-5. doi: 10.1021/ol502237a. Epub 2014 Aug 21.
7
Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO⋅(SO2)2 and hydrazines.无金属条件下 DABCO⋅(SO2)2 和肼对芳基重氮四氟硼酸盐的氨基磺酰化反应。
Angew Chem Int Ed Engl. 2014 Feb 24;53(9):2451-4. doi: 10.1002/anie.201309851. Epub 2014 Jan 29.
8
PhI(OAc)2-mediated synthesis of 6-(trifluoromethyl)phenanthridines by oxidative cyclization of 2-isocyanobiphenyls with CF3SiMe3 under metal-free conditions.PhI(OAc)2 介导的无金属条件下，用 2-异氰基联苯与 CF3SiMe3 进行氧化环化反应合成 6-(三氟甲基)菲啶。
Org Lett. 2013 Sep 20;15(18):4846-9. doi: 10.1021/ol4022589. Epub 2013 Sep 3.
9
Metal-free, visible-light-mediated direct C-H arylation of heteroarenes with aryl diazonium salts.无金属、可见光促进的杂芳烃与芳基重氮盐的直接 C-H 芳基化反应。
J Am Chem Soc. 2012 Feb 15;134(6):2958-61. doi: 10.1021/ja212099r. Epub 2012 Feb 3.
10
Hydride-induced anionic cyclization: an efficient method for the synthesis of 6-H-phenanthridines via a transition-metal-free process.氢化物诱导的阴离子环化反应：一种通过无过渡金属过程高效合成6-H-菲啶的方法。
Org Lett. 2015 Mar 20;17(6):1613-6. doi: 10.1021/acs.orglett.5b00544. Epub 2015 Mar 12.
引用本文的文献
1
Preparation of 3-hydroxyquinolines from direct oxidation of dihydroquinolinium salts.由二氢喹啉鎓盐直接氧化制备3-羟基喹啉
RSC Adv. 2018 Nov 14;8(67):38166-38174. doi: 10.1039/c8ra07940d.
2
Assembly of 1-isoindole derivatives by selective carbon-nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging.通过选择性碳氮三键活化组装1-异吲哚衍生物：用于脂滴成像的聚集诱导发光荧光团的合成方法
Chem Sci. 2019 Jun 12;10(29):7076-7081. doi: 10.1039/c9sc01035a. eCollection 2019 Aug 7.
Zotero 插件