Mapping the reactivity of the quinoline ring-system - Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers

被引:12
作者
Haheim, Katja S. [1 ]
Helgeland, Ida T. Urdal [1 ]
Lindback, Emil [1 ]
Sydnes, Magne O. [1 ]
机构
[1] Univ Stavanger, Dept Chem Biosci & Environm Engn, Fac Sci & Technol, NO-4036 Stavanger, Norway
关键词
Natural product; Suzuki-Miyaura cross-coupling; Tandem C-H activation/C-N bond formation; INDOLOQUINOLINE ALKALOIDS; H FUNCTIONALIZATION; ONE-POT; CRYPTOLEPINE; QUINAZOLINE; DERIVATIVES; ANALOGS;
D O I
10.1016/j.tet.2019.04.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bromoquinolines (2-bromoquinoline - 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C-H activation/C-N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2949 / 2957
页数:9
相关论文
共 43 条
[1]   Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines [J].
Aksenov, Alexander V. ;
Aksenov, Dmitrii A. ;
Griaznov, Georgii D. ;
Aksenov, Nicolai A. ;
Voskressensky, Leonid G. ;
Rubin, Michael .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) :4325-4332
[2]   One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine [J].
Aksenov, Alexander V. ;
Aksenov, Dmitrii A. ;
Orazova, Naila A. ;
Aksenov, Nicolai A. ;
Griaznov, Georgii D. ;
De Carvalho, Annelise ;
Kiss, Robert ;
Mathieu, Veronique ;
Kornienko, Alexander ;
Rubin, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06) :3011-3018
[3]   Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes [J].
Almond-Thynne, Joshua ;
Blakemore, David C. ;
Pryde, David C. ;
Spivey, Alan C. .
CHEMICAL SCIENCE, 2017, 8 (01) :40-62
[4]   Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents [J].
Aroonkit, Pasuk ;
Thongsornkleeb, Charnsak ;
Tummatorn, Jumreang ;
Krajangsri, Suppachai ;
Mungthin, Mathirut ;
Ruchirawat, Somsak .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 :56-62
[5]   Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C-H Activation and C-N Bond Formation [J].
Bjorsvik, Hans-Rene ;
Elumalai, Vijayaragavan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (33) :5474-5479
[6]   HALOGEN REACTIVITIES .3. KINETIC STUDY OF DISPLACEMENT REACTIONS OF HALOQUINOLINES WITH PIPERIDINE [J].
BROWER, KR ;
SAMUELS, WP ;
WAY, JW ;
AMSTUTZ, ED .
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (12) :1648-1654
[7]   Microwave irradiated acetylation of p-anisidine: A step towards green chemistry [J].
Chakraborty, Mousumi ;
Umrigar, Vaishali ;
Parikh, Parimal A. .
INTERNATIONAL JOURNAL OF CHEMICAL REACTOR ENGINEERING, 2008, 6
[8]   Visible-light-induced regioselective synthesis of polyheteroaromatic compounds [J].
Chatterjee, Tanmay ;
Choi, Myung Gil ;
Kim, Jun ;
Chang, Suk-Kyu ;
Cho, Eun Jin .
CHEMICAL COMMUNICATIONS, 2016, 52 (22) :4203-4206
[9]   THE TOTAL SYNTHESIS OF CYSTODYTINS [J].
CIUFOLINI, MA ;
BYRNE, NE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8016-8024
[10]   Active Natural Product Scaffolds against Trypanosomatid Parasites: A Review [J].
Cockram, Peter E. ;
Smith, Terry K. .
JOURNAL OF NATURAL PRODUCTS, 2018, 81 (09) :2138-2154