Syntheses of New Quinoline-Containing Heterocyclic Scaffolds Using, Inter- and Intramolecular Pd-Catalyzed Amination

被引:12
作者
Boganyi, Borbala [1 ,2 ]
Kaman, Judit [2 ]
机构
[1] Eotvos Lorand Univ, Inst Chem, Budapest, Hungary
[2] Ubichem Res, Budapest, Hungary
关键词
IN-VITRO; BENZO; CRYPTOLEPINE; DISCOVERY;
D O I
10.1002/jhet.6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tandem inter- and intramolecular Pd-catalyzed animation protocol was studied on 4-chloro-3-iodoquinoline and 3-chloro-4-iodoquinoline with different aminohetarenes. Applying this method, ten novel quinoline derivatives and eight new heterocyclic ring systems were synthesized.
引用
收藏
页码:33 / 38
页数:6
相关论文
共 14 条
[1]   Probing the N-5 region of the indoloquinoline alkaloid, cryptolepine for anticryptococcal activity [J].
Ablordeppey, SY ;
Fan, PC ;
Clark, AM ;
Nimrod, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :343-349
[2]  
Arif Jamal M, 2007, Int J Biomed Sci, V3, P194
[3]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[4]   Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities [J].
Bierer, DE ;
Fort, DM ;
Mendez, CD ;
Luo, J ;
Imbach, PA ;
Dubenko, LG ;
Jolad, SD ;
Gerber, RE ;
Litvak, J ;
Lu, Q ;
Zhang, PS ;
Reed, MJ ;
Waldeck, N ;
Bruening, RC ;
Noamesi, BK ;
Hector, RF ;
Carlson, TJ ;
King, SR .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :894-901
[5]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710
[6]   An efficient, palladium-catalysed, amination of aryl bromides [J].
Guari, Y ;
van Es, DS ;
Reek, JNH ;
Kamer, PCJ ;
van Leeuwen, PWNM .
TETRAHEDRON LETTERS, 1999, 40 (19) :3789-3790
[7]   Discovery and understanding of transition-metal-catalyzed aromatic substitution reactions [J].
Hartwig, John F. .
SYNLETT, 2006, (09) :1283-1294
[8]   Synthesis of pyrido[2′,1′: 2,3]imidazo[4,5-b] quinoline and pyrido[1′,2′:1,2]imidazo[4,5-b]quinoline and their benzo and aza analogs via tandem catalysis [J].
Loones, Kristof T. J. ;
Maes, Bert U. W. ;
Dommisse, Roger A. .
TETRAHEDRON, 2007, 63 (36) :8954-8961
[9]   The first tandem double palladium-catalyzed aminations:: synthesis of dipyrido[1,2-a:3′,2′-d]imidazole and its benzo- and aza-analogues [J].
Loones, KTJ ;
Maes, BUW ;
Dommisse, RA ;
Lemière, GLF .
CHEMICAL COMMUNICATIONS, 2004, (21) :2466-2467
[10]   Assembly of 4-aminoquinolines via palladium catalysis:: A mild and convenient alternative to SNAr methodology [J].
Margolis, Brandon J. ;
Long, Kimberly A. ;
Laird, Dana L. T. ;
Ruble, J. Craig ;
Pulley, Shon R. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :2232-2235