二溴喹啉的一锅双偶联反应研究。
Studies of one-pot double couplings on dibromoquinolines.
作者信息
Piala Alexander, Mayi Diyar, Handy Scott T
机构信息
Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37130.
出版信息
Tetrahedron. 2011 Jun 10;67(23):4147-4154. doi: 10.1016/j.tet.2011.04.052.
Abstract
In a series of studies, the regioselectivity of Suzuki couplings of dibromoquinolines has been investigated. In general, it is much harder to achieve high levels of regioselectivity in these systems compared to many of the other dibromoheteroaromatics that have been studied. Useful levels of selectivity could be achieved for both a 5,7-dibromoquinoline as well as 3,4-dibromoquinoline. Double Suzuki couplings could also be achieved on these two compounds.
摘要
在一系列研究中，对二溴喹啉的铃木偶联反应的区域选择性进行了研究。一般来说，与许多已研究的其他二溴杂芳烃相比，在这些体系中实现高水平的区域选择性要困难得多。对于5,7 - 二溴喹啉以及3,4 - 二溴喹啉都能实现有用的选择性水平。这两种化合物也能实现双铃木偶联反应。
相似文献
1
Studies of one-pot double couplings on dibromoquinolines.二溴喹啉的一锅双偶联反应研究。
Tetrahedron. 2011 Jun 10;67(23):4147-4154. doi: 10.1016/j.tet.2011.04.052.
2
Regioselective Sonogashira couplings of 2,4-dibromoquinolines. A correction.2,4-二溴喹啉的区域选择性Sonogashira偶联反应。勘误
J Org Chem. 2003 May 2;68(9):3736-8. doi: 10.1021/jo034122w.
3
Double Couplings of Dibromothiophenes using Boronic Acids and Boronates.使用硼酸和硼酸酯对二溴噻吩进行双偶联反应
Synthesis (Stuttg). 2009 May 12;40(19). doi: 10.1002/chin.200919105.
4
One-pot Double Suzuki Couplings of Dichloropyrimidines.二氯嘧啶的一锅法双铃木偶联反应
Synthesis (Stuttg). 2010 Aug 1;2010(16):2721-2724. doi: 10.1055/s-0030-1258150.
5
One-pot double Suzuki-Miyaura couplings: rapid access to nonsymmetrical tri(hetero)aryl derivatives.一锅法双铃木-宫浦偶联反应：快速合成非对称三（杂）芳基衍生物
Org Lett. 2009 Apr 16;11(8):1801-4. doi: 10.1021/ol900358n.
6
Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde.4,5-二溴噻吩-2-甲醛的区域选择性双铃木偶联反应
Tetrahedron Lett. 2007 Nov 12;48(46):8108-8110. doi: 10.1016/j.tetlet.2007.09.114.
7
Regioselective Suzuki couplings of non-symmetric dibromobenzenes: alkenes as regiochemical control elements.非对称二溴苯的区域选择性铃木偶联反应：烯烃作为区域化学控制元素
Org Biomol Chem. 2015 Jun 14;13(22):6162-5. doi: 10.1039/c5ob00717h.
8
B-Alkyl sp-sp Suzuki-Miyaura Couplings under Mild Aqueous Micellar Conditions.B-烷基 sp-sp 铃木-宫浦偶联反应在温和的胶束水溶液条件下进行。
Org Lett. 2018 May 18;20(10):2902-2905. doi: 10.1021/acs.orglett.8b00961. Epub 2018 May 8.
9
Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes.使用对称二卤代苯进行单步和双步铃木-宫浦偶联反应。
J Org Chem. 2005 Apr 29;70(9):3730-3. doi: 10.1021/jo050105q.
10
Regioselective Bromination of Thieno[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-one and Sequential Suzuki Couplings.噻吩并[2',3':4,5]吡咯并[1,2-d][1,2,4]三嗪-8(7H)-酮的区域选择性溴化及连续 Suzuki 偶联反应。
J Org Chem. 2017 Sep 1;82(17):9229-9234. doi: 10.1021/acs.joc.7b01542. Epub 2017 Aug 16.
引用本文的文献
1
Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.杂芳基卤化物的位点选择性铃木-宫浦偶联反应——了解重要药物类别中的趋势
Chem Sci. 2017 Jan 1;8(1):40-62. doi: 10.1039/c6sc02118b. Epub 2016 Aug 9.
2
Novel polycarbo-substituted alkyl (thieno[3,2-c]quinoline)-2-carboxylates: synthesis and cytotoxicity studies.新型多碳取代烷基（噻吩并[3,2-c]喹啉）-2-羧酸酯的合成与细胞毒性研究
Molecules. 2014 Nov 13;19(11):18527-42. doi: 10.3390/molecules191118527.
3
4,6,8-Triarylquinoline-3-carbaldehyde derivatives: synthesis and photophysical properties.4,6,8-三芳基喹啉-3-甲醛衍生物：合成与光物理性质。
Molecules. 2013 Dec 17;18(12):15769-87. doi: 10.3390/molecules181215769.
4
Synthesis and photophysical properties of 2-aryl-6,8-bis(arylethenyl)-4-methoxyquinolines.2-芳基-6,8-双(芳基乙烯基)-4-甲氧基喹啉的合成及光物理性质。
Molecules. 2012 Nov 30;17(12):14186-204. doi: 10.3390/molecules171214186.
本文引用的文献
1
Double Couplings of Dibromothiophenes using Boronic Acids and Boronates.使用硼酸和硼酸酯对二溴噻吩进行双偶联反应
Synthesis (Stuttg). 2009 May 12;40(19). doi: 10.1002/chin.200919105.
2
Theoretical bond dissociation energies of halo-heterocycles: trends and relationships to regioselectivity in palladium-catalyzed cross-coupling reactions.卤代杂环的理论键离解能：钯催化交叉偶联反应中的趋势及其与区域选择性的关系
J Am Chem Soc. 2009 May 13;131(18):6632-9. doi: 10.1021/ja9004927.
3
Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde.4,5-二溴噻吩-2-甲醛的区域选择性双铃木偶联反应
Tetrahedron Lett. 2007 Nov 12;48(46):8108-8110. doi: 10.1016/j.tetlet.2007.09.114.
4
Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization.
J Org Chem. 2008 Nov 7;73(21):8608-11. doi: 10.1021/jo8017654. Epub 2008 Oct 4.
5
Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates.从邻氨基苯硼酸酯进行喹啉的汇聚式、区域特异性合成。
Org Lett. 2008 Sep 18;10(18):4117-20. doi: 10.1021/ol8016726. Epub 2008 Aug 23.
6
Multiple regioselective functionalizations of quinolines via magnesiations.通过镁化反应实现喹啉的多区域选择性官能团化
Org Lett. 2007 Dec 20;9(26):5525-8. doi: 10.1021/ol702494k. Epub 2007 Nov 21.
7
Disubstituted pyridines: the double-coupling approach.二取代吡啶：双偶联方法。
J Org Chem. 2007 Oct 26;72(22):8496-500. doi: 10.1021/jo701709a. Epub 2007 Oct 5.
8
Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions.在微波辅助条件下，通过金（I）催化的串联氢胺化-氢芳基化反应，由芳香胺和炔烃合成取代的1,2-二氢喹啉和喹啉。
Org Lett. 2007 Jul 5;9(14):2645-8. doi: 10.1021/ol070814l. Epub 2007 Jun 12.
9
N',2-diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists.
Bioorg Med Chem Lett. 2006 Nov 15;16(22):5748-51. doi: 10.1016/j.bmcl.2006.08.086. Epub 2006 Sep 6.
10
Molecular fluorescent pH-probes based on 8-hydroxyquinoline.基于8-羟基喹啉的分子荧光pH探针。
Org Biomol Chem. 2006 Apr 21;4(8):1503-11. doi: 10.1039/b600912c. Epub 2006 Mar 14.
Zotero 插件