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

来源：

TETRAHEDRON | 2019年 / 75卷 / 21期

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

页码：2949 / 2957

页数：9

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

← 1 2 3 4 5 →