Synthesis of spiroquinolines through a one-pot multicatalytic and multicomponent cascade reaction

被引:72
作者
Barluenga, Jose [1 ]
Mendoza, Abraham [1 ]
Rodriguez, Felix [1 ]
Fananas, Francisco J. [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33006 Oviedo, Spain
关键词
cyclization; homogeneous catalysis; multicomponent; reactions; platinum; quinolines;
D O I
10.1002/anie.200802582
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Three's company: Functionalized spirocyclic quinoline derivatives are easily synthesized in a one-pot three-component coupling process involving the reaction of alkynol, aldehyde, and aniline derivatives (see scheme). The process is carried out in the presence of catalytic amounts of a platinum(II) complex and a protic acid. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7044 / 7047
页数:4
相关论文
共 59 条
  • [31] Hashmi ASK, 2004, GOLD BULL, V37, P51
  • [32] Potent in vitro methicillin-resistant Staphylococcus aureus activity of 2-(1H-indol-3-yl)tetrahydroquinoline derivatives
    Hoemann, MZ
    Xie, RL
    Rossi, RF
    Meyer, S
    Sidhu, A
    Cuny, GD
    Hauske, JR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (02) : 129 - 132
  • [33] The golden gate to catalysis
    Hoffmann-Röder, A
    Krause, N
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) : 387 - 391
  • [34] Molecular diversity through gold catalysis with alkynes
    Jimenez-Nunez, Eloisa
    Echavarren, Antonio M.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (04) : 333 - 346
  • [35] Facile synthesis of tetrahydroquinolines and julolidines through multicomponent reaction
    Legros, Julien
    Crousse, Benoit
    Ourevitch, Michele
    Bonnet-Delpon, Daniele
    [J]. SYNLETT, 2006, (12) : 1899 - 1902
  • [36] Metal-catalyzed regioselective oxy-functionalization of internal alkynes: An entry into ketones, acetals, and spiroketals
    Liu, Bo
    De Brabander, Jef K.
    [J]. ORGANIC LETTERS, 2006, 8 (21) : 4907 - 4910
  • [37] Insight into the selective room-temperature platinum(II) catalytic hydration of alkynes in water
    Lucey, DW
    Atwood, JD
    [J]. ORGANOMETALLICS, 2002, 21 (12) : 2481 - 2490
  • [38] Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels-Alder reactions under solvent-free conditions:: a facile synthesis of trans-fused pyrano- and furanotetrahydroquinolines
    Nagaiah, K.
    Sreenu, D.
    Rao, R. Srinivasa
    Vashishta, G.
    Yadav, J. S.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (26) : 4409 - 4413
  • [39] VIRANTMYCIN - A NEW ANTIVIRAL ANTIBIOTIC PRODUCED BY A STRAIN OF STREPTOMYCES
    NAKAGAWA, A
    IWAI, Y
    HASHIMOTO, H
    MIYAZAKI, N
    OIWA, R
    TAKAHASHI, Y
    HIRANO, A
    SHIBUKAWA, N
    KOJIMA, Y
    OMURA, S
    [J]. JOURNAL OF ANTIBIOTICS, 1981, 34 (11) : 1408 - 1415
  • [40] Synthesis of multisubstituted 2-(dihydrofuran-2(3H)-ylidene)acetates via intramolecular carboalkoxylation by platinum-olefin catalyst system
    Nakamura, Itaru
    Chan, Ching Siew
    Araki, Toshiharu
    Terada, Masahiro
    Yamamoto, Yoshinori
    [J]. ORGANIC LETTERS, 2008, 10 (02) : 309 - 312