Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids

被引：2
作者：
Mphahlele, Malose Jack [1 ]
Mphahlele, Mamasegare Mabel [1 ]
机构：
[1] Univ S Africa, Dept Chem, Coll Sci Engn & Technol, ZA-0003 Pretoria, South Africa
来源：
MOLECULES | 2011年 / 16卷 / 11期
基金：
新加坡国家研究基金会;
关键词：
2-aryl-4-azido-3-iodoquinolines; Suzuki-Miyaura cross-coupling; symmetrical biaryls; 4-azido-2,3-diarylquinolines; 4-amino-2,3-diarylquinolines; PALLADIUM; DERIVATIVES; MOLECULES; DISCOVERY;
D O I：
10.3390/molecules16118958
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed.
引用
收藏
页码：8958 / 8972
页数：15
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共 37 条
  • [1] A new application of diphenylphosphorylazide (DPPA) reagent: convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts
    Aizikovich, A
    Kuznetsov, V
    Gorohovsky, S
    Levy, A
    Meir, S
    Byk, G
    Gellerman, G
    [J]. TETRAHEDRON LETTERS, 2004, 45 (22) : 4241 - 4243
  • [2] A SHORT NEW ROUTE TO THE PYRIDO[2,3,4-KL]ACRIDINE SUBUNIT COMMON TO PYRIDOACRIDINE ALKALOIDS OF MARINE ORIGIN
    ALI, NM
    CHATTOPADHYAY, SK
    MCKILLOP, A
    PERRETGENTIL, RM
    OZTURK, T
    REBELO, RA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (19) : 1453 - 1454
  • [3] Mechanistic and kinetic studies of palladium catalytic systems
    Amatore, C
    Jutand, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 254 - 278
  • [4] A mild and efficient one-step synthesis of quinolines
    De, SK
    Gibbs, RA
    [J]. TETRAHEDRON LETTERS, 2005, 46 (10) : 1647 - 1649
  • [5] Synthesis and SAR of aminoalkoxy-biaryl-4-carboxamides:: Novel and selective histamine H3 receptor antagonists
    Faghih, R
    Dwight, W
    Pan, JB
    Fox, GB
    Krueger, KM
    Esbenshade, TA
    McVey, JM
    Marsh, K
    Bennani, YL
    Hancock, AA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (07) : 1325 - 1328
  • [6] Highly chemoselective hydrogenolysis of iodoarenes
    Faucher, N
    Ambroise, Y
    Cintrat, JC
    Doris, E
    Pillon, F
    Rousseau, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) : 932 - 934
  • [7] Alkylation of 2-phenyl-4-quinolones: Synthetic and structural studies
    Hadjeri, M
    Mariotte, AM
    Boumendjel, A
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (10) : 1352 - 1355
  • [8] Privileged molecules for protein binding identified from NMR-based screening
    Hajduk, PJ
    Bures, M
    Praestgaard, J
    Fesik, SW
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (18) : 3443 - 3447
  • [9] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates
    Hamann, BC
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7369 - 7370
  • [10] Elucidating reactivity differences in palladium-catalyzed coupling processes: The chemistry of palladium hydrides
    Hills, ID
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (41) : 13178 - 13179
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