Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine

被引:22
作者
Abbiati, Giorgio [1 ]
Arcadi, Antonio [2 ]
Canevaria, Valentina [1 ]
Rossia, Elisabetta [1 ]
机构
[1] Univ Milan, Fac Farm, Ist Chim Organ Alessandro Marchesini, I-20133 Milan, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Coppito, AQ, Italy
关键词
imidazole; amidine; alkynes; homogeneous catalysis; palladium; Domino reaction; aminopalladation;
D O I
10.1016/j.tetlet.2007.09.153
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preliminary results of an original approach to 4-substituted-2-phenylimidazoles starting from readily available N-propargyl-benzamidine and aryl halides are reported. Best yields were obtained using aryl halides bearing an electron-withdrawing group. Plausible mechanisms are also discussed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8491 / 8495
页数:5
相关论文
共 44 条
  • [1] Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates
    Abbiati, G
    Arcadi, A
    Beccalli, E
    Bianchi, G
    Marinelli, F
    Rossi, E
    [J]. TETRAHEDRON, 2006, 62 (13) : 3033 - 3039
  • [2] Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles:: a new entry to [1,4]oxazino[4,3-a]indoles
    Abbiati, G
    Canevari, V
    Caimi, S
    Rossi, E
    [J]. TETRAHEDRON LETTERS, 2005, 46 (42) : 7117 - 7120
  • [3] Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles
    Abbiati, G
    Arcadi, A
    Bellinazzi, A
    Beccalli, E
    Rossi, E
    Zanzola, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) : 4088 - 4095
  • [4] Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines
    Abbiati, Giorgio
    Arcadi, Antonio
    Marinelli, Fabio
    Rossi, Ellsabetta
    Verdecchia, Mirella
    [J]. SYNLETT, 2006, (19) : 3218 - 3224
  • [5] TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes
    Abbiati, Giorgio
    Casoni, Alessandro
    Canevari, Valentina
    Nava, Donatella
    Rossi, Elisabetta
    [J]. ORGANIC LETTERS, 2006, 8 (21) : 4839 - 4842
  • [6] TiCl4-Catalyzed indirect anti-markovnikov hydration of alkynes:: Application to the synthesis of benzo[b]furans
    Ackermann, Lutz
    Kaspar, Ludwig T.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) : 6149 - 6153
  • [7] 2,3-Disubstituted pyrrolo[2,3-b]quinoxalines via aminopalladation-reductive elimination
    Arcadi, A
    Cacchi, S
    Fabrizi, G
    Parisi, LM
    [J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2431 - 2434
  • [8] Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO
  • [9] 2-R
  • [10] Highly substituted furans from 2-propynyl-1,3-dicarbonyls and organic halides or triflates via the oxypalladation-reductive elimination domino reaction
    Arcadi, A
    Cacchi, S
    Fabrizi, G
    Marinelli, F
    Parisi, LM
    [J]. TETRAHEDRON, 2003, 59 (25) : 4661 - 4671