The Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles

被引:32
|
作者
Roy, PJ [1 ]
Dufresne, C [1 ]
Lachance, N [1 ]
Leclerc, JP [1 ]
Boisvert, M [1 ]
Wang, ZY [1 ]
Leblanc, Y [1 ]
机构
[1] Merck Frosst Ctr Therapeut Res, Pointe Claire, PQ H9R 4P8, Canada
来源
SYNTHESIS-STUTTGART | 2005年 / 16期
关键词
Hemetsberger-Knittel reaction; azaindoles; thermolysis; cyclization; template;
D O I
10.1055/s-2005-872165
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a mininium ternperature. The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chemical diversity.
引用
收藏
页码:2751 / 2757
页数:7
相关论文
共 50 条
  • [41] Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates
    Nuhant, Philippe
    Allais, Christophe
    Chen, Ming Z.
    Coe, Jotham W.
    Dermenci, Alpay
    Fadeyi, Olugbeminiyi O.
    Flick, Andrew C.
    Mousseau, James J.
    ORGANIC LETTERS, 2015, 17 (17) : 4292 - 4295
  • [42] Synthesis of 4-(cyclic dialkylamino)-7-azaindoles by microwave heating of 4-halo-7-azaindoles and cyclic secondary amines
    Caldwell, John J.
    Cheung, Kwal-Ming
    Collins, Ian
    TETRAHEDRON LETTERS, 2007, 48 (09) : 1527 - 1529
  • [43] Discovery of N-substituted 7-azaindoles as PIM1 kinase inhibitors - Part I
    Barberis, Claude
    Moorcroft, Neil
    Arendt, Chris
    Levit, Mikhail
    Moreno-Mazza, Sandra
    Batchelor, Joseph
    Mechin, Ingrid
    Majid, Tahir
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (20) : 4730 - 4734
  • [44] Synthesis of Cycloalkyl Substituted 7-Azaindoles via Photoredox Nickel Dual Catalytic Cross-Coupling in Batch and Continuous Flow
    Palaychuk, Natalie
    DeLano, Travis J.
    Boyd, Michael J.
    Green, Jeremy
    Bandarage, Upul K.
    ORGANIC LETTERS, 2016, 18 (23) : 6180 - 6183
  • [45] DERIVATIVES OF AZAINDOLES .51. SYNTHESIS OF SUBSTITUTED (7-AZAINDOLINYL-6)DIPHENYLCARBINOLES
    KRASNOKUTSKAYA, DM
    MORKOVNIK, AS
    TERTOV, BA
    YAKHONTOV, LN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (11): : 1527 - 1530
  • [46] Concerning the reaction ability of 5-, 6-, 7-(enamino)indoles at synthesis of pyrroloquinolines
    Yamashkin, SA
    Trushkov, IV
    Tomilin, OB
    Terekhin, II
    Yurovskaya, MA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (09): : 1223 - 1242
  • [47] SUGAR LACTAMS .3. SYNTHESIS OF 5- 6- AND 7-MEMBERED ANALOGS
    HANESSIAN, S
    JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03): : 675 - +
  • [48] SYNTHESIS OF SUBSTITUTED 4- AND 6-AZAINDOLES
    FRYDMAN, B
    REIL, SJ
    BONED, J
    RAPOPORT, H
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10): : 3762 - &
  • [49] Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles
    Mahiout, Zahia
    Lomberget, Thierry
    Goncalves, Sylvie
    Barret, Roland
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (08) : 1364 - 1376
  • [50] DERIVATIVES OF AZAINDOLES .55. SYNTHESIS OF 3-SUBSTITUTED 6-AZAINDOLES
    PROKOPOV, AA
    YAKHONTOV, LN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (04): : 496 - 500