通过肼催化的闭环羰基-烯烃复分解反应合成 1,2-二氢喹啉。
Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.
机构信息
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
出版信息
Org Lett. 2020 Aug 7;22(15):6026-6030. doi: 10.1021/acs.orglett.0c02116. Epub 2020 Jul 15.
Abstract
The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of -prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.
摘要
本文报道了通过肼催化的 -prenylated 2-氨基苯甲醛的闭环羰基-烯烃复分解反应（RCCOM）合成 1,2-二氢喹啉。展示了具有各种取代模式的底物。氮原子上带有酸不稳定保护基时，可进行原位脱保护和自动氧化生成喹啉。与相关含氧底物相比，催化循环的环加成步骤较慢，但发现环重排更容易。
相似文献
1
Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.通过肼催化的闭环羰基-烯烃复分解反应合成 1,2-二氢喹啉。
Org Lett. 2020 Aug 7;22(15):6026-6030. doi: 10.1021/acs.orglett.0c02116. Epub 2020 Jul 15.
2
Synthesis of 2-Chromenes via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.通过肼催化的闭环羰基-烯烃复分解反应合成2-色烯
ACS Catal. 2019 Oct 4;9(10):9259-9264. doi: 10.1021/acscatal.9b03656. Epub 2019 Sep 10.
3
Carbonyl-Olefin Metathesis.羰基-烯烃复分解反应。
Chem Rev. 2021 Aug 11;121(15):9359-9406. doi: 10.1021/acs.chemrev.0c01096. Epub 2021 Jun 16.
4
Organocatalytic carbonyl-olefin metathesis.有机催化羰基-烯烃复分解反应。
J Am Chem Soc. 2012 Nov 14;134(45):18581-4. doi: 10.1021/ja309650u. Epub 2012 Nov 5.
5
Ring-opening carbonyl-olefin metathesis of norbornenes.降冰片烯的开环羰基-烯烃复分解反应
Chem Sci. 2020 Jul 1;11(30):7884-7895. doi: 10.1039/d0sc02243h.
6
Polycyclic heteroaromatics hydrazine-catalyzed ring-closing carbonyl-olefin metathesis.多环杂芳烃 肼催化的闭环羰基-烯烃复分解反应
Chem Sci. 2022 Feb 1;13(8):2418-2422. doi: 10.1039/d1sc06234d. eCollection 2022 Feb 23.
7
Synthesis of 3-hydroxypyridines using ruthenium-catalyzed ring-closing olefin metathesis.使用钌催化的闭环烯烃复分解反应合成3-羟基吡啶。
Org Lett. 2009 Feb 5;11(3):515-8. doi: 10.1021/ol8023117.
8
Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction.铁(III)催化的羰基-烯烃复分解反应的机理研究。
J Am Chem Soc. 2017 Aug 9;139(31):10832-10842. doi: 10.1021/jacs.7b05641. Epub 2017 Jul 28.
9
GaCl-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis.GaCl 催化的开环羰基-烯烃复分解反应。
Org Lett. 2018 Aug 17;20(16):4954-4958. doi: 10.1021/acs.orglett.8b02086. Epub 2018 Jul 27.
10
Sequential N-acylamide methylenation-enamide ring-closing metathesis: construction of benzo-fused nitrogen heterocycles.顺序N-酰基酰胺亚甲基化-烯酰胺闭环复分解反应：苯并稠合氮杂环的构建
J Org Chem. 2006 Sep 1;71(18):7028-34. doi: 10.1021/jo061180j.
引用本文的文献
1
Theoretical Investigations of Substrate Behavior in FeCl-Catalyzed Carbonyl-Olefin Metathesis.FeCl催化的羰基-烯烃复分解反应中底物行为的理论研究
ACS Omega. 2025 Mar 6;10(10):10283-10293. doi: 10.1021/acsomega.4c09880. eCollection 2025 Mar 18.
2
Cyclization Strategies in Carbonyl-Olefin Metathesis: An Up-to-Date Review.羰基-烯烃复分解反应中的环化策略：最新综述
Molecules. 2024 Oct 14;29(20):4861. doi: 10.3390/molecules29204861.
3
Hydrazine-Catalysed Ring-Opening Metathesis Polymerization Of Cyclobutenes.肼催化的环丁烯开环易位聚合反应
Angew Chem Int Ed Engl. 2024 Dec 20;63(52):e202413093. doi: 10.1002/anie.202413093. Epub 2024 Oct 22.
4
Diazene-Catalyzed Oxidative Alkyl Halide-Olefin Metathesis.重氮催化的氧化卤代烃-烯烃复分解反应
Org Lett. 2024 Feb 9;26(5):1078-1082. doi: 10.1021/acs.orglett.3c04309. Epub 2024 Jan 31.
5
Autoxidation of 4-Hydrazinylquinolin-2(1)-one; Synthesis of Pyridazino[4,3-:5,6-']diquinoline-6,7(5,8)-diones.4-肼基喹啉-2(1H)-酮的自动氧化；哒嗪并[4,3-:5,6-']二喹啉-6,7(5,8)-二酮的合成。
Molecules. 2022 Mar 25;27(7):2125. doi: 10.3390/molecules27072125.
6
Polycyclic heteroaromatics hydrazine-catalyzed ring-closing carbonyl-olefin metathesis.多环杂芳烃 肼催化的闭环羰基-烯烃复分解反应
Chem Sci. 2022 Feb 1;13(8):2418-2422. doi: 10.1039/d1sc06234d. eCollection 2022 Feb 23.
7
Hydrogen Bonding Networks Enable Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis.氢键网络助力布朗斯特酸催化的羰基-烯烃复分解反应。
Angew Chem Int Ed Engl. 2022 Mar 21;61(13):e202117366. doi: 10.1002/anie.202117366. Epub 2022 Feb 10.
8
Carbonyl-Olefin Metathesis.羰基-烯烃复分解反应。
Chem Rev. 2021 Aug 11;121(15):9359-9406. doi: 10.1021/acs.chemrev.0c01096. Epub 2021 Jun 16.
本文引用的文献
1
Synthesis of 2-Chromenes via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.通过肼催化的闭环羰基-烯烃复分解反应合成2-色烯
ACS Catal. 2019 Oct 4;9(10):9259-9264. doi: 10.1021/acscatal.9b03656. Epub 2019 Sep 10.
2
Recent Progress in the Synthesis of Quinolines.喹啉合成的最新进展
Curr Org Synth. 2019;16(5):671-708. doi: 10.2174/1570179416666190719112423.
3
Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation.通过镓催化的串联羰基-烯烃复分解/转移氢化反应合成中碳环。
Org Lett. 2019 Oct 4;21(19):8132-8137. doi: 10.1021/acs.orglett.9b03240. Epub 2019 Sep 23.
4
Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow.在流动相中，均相和固态酸催化的乙烯基醚的分子间羰基-烯烃复分解反应。
Angew Chem Int Ed Engl. 2020 Mar 2;59(10):3846-3849. doi: 10.1002/anie.201909597. Epub 2019 Oct 4.
5
Catalyst Behavior in Metal-Catalyzed Carbonyl-Olefin Metathesis.金属催化的羰基-烯烃复分解中的催化剂行为。
J Am Chem Soc. 2019 Jul 31;141(30):11870-11880. doi: 10.1021/jacs.9b02613. Epub 2019 Jul 22.
6
Catalytic Isofunctional Reactions-Expanding the Repertoire of Shuttle and Metathesis Reactions.催化同功能反应——拓展穿梭和复分解反应的应用范围。
Angew Chem Int Ed Engl. 2019 Jul 22;58(30):10074-10103. doi: 10.1002/anie.201803797. Epub 2019 Apr 30.
7
Lewis Acid Catalyzed Carbonyl-Olefin Metathesis.路易斯酸催化的羰基-烯烃复分解反应
Synlett. 2017;28(13):1501-1509. doi: 10.1055/s-0036-1588827.
8
Tropylium-promoted carbonyl-olefin metathesis reactions.环庚三烯正离子促进的羰基-烯烃复分解反应。
Chem Sci. 2018 May 4;9(23):5145-5151. doi: 10.1039/c8sc00907d. eCollection 2018 Jun 21.
9
Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host.自组装超分子主体内的布朗斯特酸催化的羰基-烯烃复分解反应
Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14589-14592. doi: 10.1002/anie.201712141. Epub 2018 Jan 11.
10
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis.通过铁（III）催化的羰基-烯烃复分解反应生成多环芳烃。
J Am Chem Soc. 2017 Mar 1;139(8):2960-2963. doi: 10.1021/jacs.7b01114. Epub 2017 Feb 21.
Zotero 插件