A novel Zn-catalyzed hydroamination of propargylamides: a general synthesis of di- and tri-substituted imidazoles

被引:32
作者
Pews-Davtyan, Anahit [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
ONE-POT SYNTHESIS; TERMINAL ALKYNES; INTERMOLECULAR HYDROAMINATION; MILD CONDITIONS; C-C; DERIVATIVES; CYCLIZATION; FUNCTIONALIZATION; 1H-IMIDAZOLES; HETEROCYCLES;
D O I
10.1039/c0cc04625f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from commercially available amines and propargyl-amides a variety of substituted imidazoles were synthesized via a novel hydroamination-cyclization sequence. The target compounds are obtained in good to excellent yields in the presence of catalytic amounts of zinc triflate.
引用
收藏
页码:2152 / 2154
页数:3
相关论文
共 57 条
  • [1] Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine
    Abbiati, Giorgio
    Arcadi, Antonio
    Canevaria, Valentina
    Rossia, Elisabetta
    [J]. TETRAHEDRON LETTERS, 2007, 48 (48) : 8491 - 8495
  • [2] Gold(III) iminophosphorane complexes as catalysts in C-C and C-O bond formations
    Aguilar, David
    Contel, Maria
    Navarro, Rafael
    Soler, Tatiana
    Urriolabeitia, Esteban P.
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) : 486 - 493
  • [3] Alanine A., 2002, WO 02060877, Patent No. 02060877
  • [4] Alex K., 2008, Angew. Chem, V120, P2337
  • [5] General zinc-catalyzed intermolecular hydroamination of terminal alkynes
    Alex, Karolin
    Tillack, Annegret
    Schwarz, Nicolle
    Beller, Matthias
    [J]. CHEMSUSCHEM, 2008, 1 (04) : 333 - 338
  • [6] Almstetter M., 2010, WO 2010026212, Patent No. 2010026212
  • [7] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [8] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    Beller, M
    Seayad, J
    Tillack, A
    Jiao, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
  • [9] Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles
    Bellina, Fabio
    Cauteruccio, Silvia
    Rossi, Renzo
    [J]. TETRAHEDRON, 2007, 63 (22) : 4571 - 4624
  • [10] Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed C-N and C-C Bond Forming Reactions
    Bellina, Fabio
    Rossi, Renzo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1223 - 1276