Facile synthesis of 4-and 7-azaindoles from the corresponding imines by palladium-catalyzed cascade C-C and C-N coupling

被引:21
|
作者
Ngo Nghia Pham [1 ,2 ]
Thanh Tuan Dang [1 ]
Ngoc Thang Ngo [1 ,3 ]
Villinger, Alexander [1 ]
Ehlers, Peter [1 ]
Langer, Peter [1 ,3 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] VNU Univ Sci Hanoi VNU HUS, Fac Chem, Hanoi, Vietnam
[3] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
ONE-POT SYNTHESIS; PHASE SYNTHESIS; ARYL IMINES; AZAINDOLE; DESIGN; 7-AZATRYPTOPHAN; HYDROGENATION; OPTIMIZATION; INHIBITORS; 4-AZAINDOLES;
D O I
10.1039/c5ob00720h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclization of 2,3-dihalopyridines with readily available imines provides a convenient and regioselective approach to 4- and 7-azaindoles. The regioselectivity can be controlled by the choice of the halogen atoms at the pyridine ring (chlorine versus bromine).
引用
收藏
页码:6047 / 6058
页数:12
相关论文
共 50 条
  • [41] Classical Reagents: New Surprises in Palladium-Catalyzed C-C Coupling Reactions
    Lindhardt, Anders T.
    Skrydstrup, Troels
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (29) : 8756 - 8766
  • [42] Bioconjugation of peptides by palladium-catalyzed C-C cross-coupling in water
    Dibowski, H
    Schmidtchen, FP
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (04) : 476 - 478
  • [43] Palladium catalyzed C-C and C-N bond forming reactions: an update on the synthesis of pharmaceuticals from 2015-2020
    Rayadurgam, Jayachandra
    Sana, Sravani
    Sasikumar, M.
    Gu, Qiong
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (02) : 384 - 414
  • [44] Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
    Surasani, Rajendra
    Kalita, Dipak
    Rao, A. V. Dhanunjaya
    Chandrasekhar, K. B.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 2004 - 2018
  • [45] Palladium-catalyzed C-N and C-C cross-couplings as versatile, new avenues for modifications of purine 2'-deoxynucleosides
    Lakshman, MK
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) : 234 - 251
  • [46] Synthesis of C-N or C-C Spiroindolines via Rearrangement Coupling Reaction
    Liu, Xiaoling
    Qiao, Panpan
    Chen, Hui
    Gao, Yu
    Chen, Haijun
    ORGANIC LETTERS, 2024, 26 (45) : 9759 - 9763
  • [47] ortho,ortho′-Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium-Catalyzed C-C and C-N Bond Formation
    Doherty, Simon
    Knight, Julian G.
    McGrady, John P.
    Ferguson, Alexandra M.
    Ward, Nicholas A. B.
    Harrington, Ross W.
    Clegg, William
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) : 201 - 211
  • [48] Palladium-catalyzed C-C bond cleavage of N-cyclopropyl acylhydrazones
    Fujioka, Hiroki
    Yasui, Motohiro
    Hamada, Shohei
    Fukumi, Kohei
    Takeda, Norihiko
    Kobayashi, Yusuke
    Furuta, Takumi
    Ueda, Masafumi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (16) : 3262 - 3267
  • [49] The synthesis of N-arylcyclopropylamines via palladium-catalyzed C-N bond formation
    Cui, W
    Loeppky, RN
    TETRAHEDRON, 2001, 57 (15) : 2953 - 2956
  • [50] Palladium-Catalyzed C-N Cross-Coupling of N′-Monosubstituted Sulfondiimines with Aryl Bromides
    Candy, Mathieu
    Bohmann, Rebekka Anna
    Bolm, Carsten
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2928 - 2932