通过N-（2-炔基）苯胺的亲电环化反应合成取代喹啉
Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.
作者信息
Zhang Xiaoxia, Yao Tuanli, Campo Marino A, Larock Richard C
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011.
出版信息
Tetrahedron. 2010 Feb 6;66(6):1177. doi: 10.1016/j.tet.2009.12.012.
Abstract
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I(2), Br(2), PhSeBr and p-O(2)NC(6)H(4)SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)(2)-catalyzed ring closure of these same alkynylanilines.
摘要
通过N-(2-炔基)苯胺与ICl、I₂、Br₂、PhSeBr和对硝基苯磺酰氯进行6-内型亲电环化反应，可在温和的反应条件下轻松合成多种取代喹啉。在各种官能团存在的情况下，该反应能以中等至良好的产率得到含3-卤素、硒和硫的喹啉。通过这些相同的炔基苯胺在Hg(OTf)₂催化下闭环反应，已合成了在3-位带有氢原子的类似喹啉。
相似文献
1
Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.通过N-（2-炔基）苯胺的亲电环化反应合成取代喹啉
Tetrahedron. 2010 Feb 6;66(6):1177. doi: 10.1016/j.tet.2009.12.012.
2
Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes.通过亚氨基炔烃的亲电环化反应合成取代异喹啉。
J Org Chem. 2002 May 17;67(10):3437-44. doi: 10.1021/jo020020e.
3
Synthesis of 5-iodopyrrolo[1,2-a]quinolines and indolo[1,2-a]quinolines via iodine-mediated electrophilic and regioselective 6-endo-dig ring closure.通过碘介导的亲电和区域选择性 6-endo-环闭合反应合成 5-碘吡咯并[1,2-a]喹啉和吲哚并[1,2-a]喹啉。
J Org Chem. 2011 Jul 15;76(14):5670-84. doi: 10.1021/jo200638k. Epub 2011 Jun 16.
4
Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines.通过N-（2-炔基）苯胺的亲电环化反应合成取代喹啉。
Org Lett. 2005 Mar 3;7(5):763-6. doi: 10.1021/ol0476218.
5
Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.通过炔烃的亲电环化反应合成萘和2-萘酚。
J Org Chem. 2006 Jan 6;71(1):236-43. doi: 10.1021/jo051948k.
6
Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.通过钯催化的末端炔烃偶联和亲电环化反应合成2,3-二取代苯并[b]噻吩
J Org Chem. 2002 Mar 22;67(6):1905-9. doi: 10.1021/jo011016q.
7
Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones.通过炔醛和炔酮的亲电环化高效合成杂环和碳环。
Org Lett. 2004 May 13;6(10):1581-4. doi: 10.1021/ol049690s.
8
Synthesis of polycyclic aromatics and heteroaromatics via electrophilic cyclization.通过亲电环化合成多环芳烃和杂芳烃。
J Org Chem. 2005 Apr 29;70(9):3511-7. doi: 10.1021/jo050104y.
9
Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.通过N，N-二烷基-2-（1-炔基）苯胺的亲电环化合成3-碘吲哚。
Org Lett. 2004 Mar 18;6(6):1037-40. doi: 10.1021/ol0498996.
10
Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization.通过亲电环化合成异香豆素和α-吡喃酮。
J Org Chem. 2003 Jul 25;68(15):5936-42. doi: 10.1021/jo034308v.
引用本文的文献
1
NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study.一锅法中NBS介导的四氢喹啉溴化与脱氢反应：范围及机理研究
RSC Adv. 2023 Nov 15;13(47):33495-33499. doi: 10.1039/d3ra06747e. eCollection 2023 Nov 7.
2
Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes.炔丙胺的高选择性环化和异构化反应以合成官能化喹啉和1-氮杂二烯。
Molecules. 2023 Aug 26;28(17):6259. doi: 10.3390/molecules28176259.
3
Synthesis and crystal structures of ()-'-(4-chloro-3-nitro-benzyl-idene)acetohydrazide and ()-2-(4-chloro-benzyl-idene)-1-(quinolin-8-yl)hydrazine.（）-‘-（4-氯-3-硝基-亚苄基）乙酰肼和（）-2-（4-氯-亚苄基）-1-（喹啉-8-基）肼的合成与晶体结构
Acta Crystallogr E Crystallogr Commun. 2023 Jul 28;79(Pt 8):762-766. doi: 10.1107/S2056989023006412. eCollection 2023 Jul 1.
4
Rational Design and Facile Synthesis of a Highly Tunable Quinoline-Based Fluorescent Small-Molecule Scaffold for Live Cell Imaging.理性设计与简便合成一种基于喹啉的荧光小分子骨架，用于活细胞成像的高可调性。
J Am Chem Soc. 2018 Aug 1;140(30):9486-9493. doi: 10.1021/jacs.8b03738. Epub 2018 Jul 20.
5
Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.铜催化 1,3-二烯与 3-溴吡啶的杂芳基硼化反应：协同取代。
Angew Chem Int Ed Engl. 2018 May 22;57(21):6146-6149. doi: 10.1002/anie.201801139. Epub 2018 Apr 26.
6
Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.通过烯醇对甲苯磺酰化和铃木-宫浦偶联反应高立体选择性合成四取代非环全碳烯烃。
J Am Chem Soc. 2017 Aug 9;139(31):10777-10783. doi: 10.1021/jacs.7b05071. Epub 2017 Jul 26.
7
Catalyst Controlled Regiodivergent Arylboration of Dienes.催化剂控制的二烯芳烃区域选择性硼化反应。
J Am Chem Soc. 2017 Jul 26;139(29):9823-9826. doi: 10.1021/jacs.7b05477. Epub 2017 Jul 12.
8
Recent Advances in Metal-Free Quinoline Synthesis.无金属喹啉合成的最新进展
Molecules. 2016 Jul 29;21(8):986. doi: 10.3390/molecules21080986.
9
Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.钯催化的丁二烯 1,4-双官能化反应形成缺碳多烯。
J Am Chem Soc. 2013 Mar 20;135(11):4167-70. doi: 10.1021/ja3110544. Epub 2013 Mar 12.
10
A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.钯催化的共轭二烯或末端烯烃与乙烯基三氟甲磺酸酯和硼酸的三组分交叉偶联反应。
J Am Chem Soc. 2011 Apr 20;133(15):5784-7. doi: 10.1021/ja201358b. Epub 2011 Mar 30.
本文引用的文献
1
Solid-phase synthesis of 1,2,3-trisubstituted indoles and 2,3-disubstituted benzofurans via iodocyclization.通过碘环化反应固相合成1,2,3-三取代吲哚和2,3-二取代苯并呋喃。
J Comb Chem. 2005 Nov-Dec;7(6):809-12. doi: 10.1021/cc050062r.
2
New iodination reactions of saturated hydrocarbons.
Angew Chem Int Ed Engl. 2005 Sep 12;44(36):5851-4. doi: 10.1002/anie.200501195.
3
Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines.通过N-（2-炔基）苯胺的亲电环化反应合成取代喹啉。
Org Lett. 2005 Mar 3;7(5):763-6. doi: 10.1021/ol0476218.
4
Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization.通过亲电环化反应实现异吲哚啉-1-酮的区域和立体选择性合成。
J Org Chem. 2005 Feb 18;70(4):1432-7. doi: 10.1021/jo048007c.
5
Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles.羰基与炔烃在与IPy2BF4反应时发生环化，并被亲核试剂捕获：一种用于组装含氧杂环的通用引发剂。
J Am Chem Soc. 2003 Jul 30;125(30):9028-9. doi: 10.1021/ja0355372.
6
Synthesis of polycyclic aromatic iodides via ICl-induced intramolecular cyclization.通过ICl诱导的分子内环化合成多环芳基碘化物。
Org Lett. 2004 Aug 5;6(16):2677-80. doi: 10.1021/ol049161o.
7
Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones.通过炔醛和炔酮的亲电环化高效合成杂环和碳环。
Org Lett. 2004 May 13;6(10):1581-4. doi: 10.1021/ol049690s.
8
Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.通过N，N-二烷基-2-（1-炔基）苯胺的亲电环化合成3-碘吲哚。
Org Lett. 2004 Mar 18;6(6):1037-40. doi: 10.1021/ol0498996.
9
Ru(III)-catalyzed cyclization of arene-alkene substrates via intramolecular electrophilic hydroarylation.钌（III）催化芳烃-烯烃底物通过分子内亲电氢芳基化反应进行环化。
Org Lett. 2004 Feb 19;6(4):581-4. doi: 10.1021/ol036385i.
10
Mercuric triflate-(TMU)3-catalyzed cyclization of omega-arylalkyne leading to dihydronaphthalenes.三氟甲磺酸汞-(TMU)3催化ω-芳基炔烃环化生成二氢萘。
Org Lett. 2003 Nov 27;5(24):4563-5. doi: 10.1021/ol035622e.
Zotero 插件