Diversity-Oriented Silver(I)-Mediated Synthesis of Spiro-2-aminoimidazoles

被引:18
作者
Pereshivko, Olga P. [1 ]
Peshkov, Vsevolod A. [1 ]
Ermolat'ev, Denis S. [1 ]
Van Hove, Sofie [1 ]
Van Hecke, Kristof
Van Meervelt, Luc
Van der Eycken, Erik V. [1 ]
机构
[1] Katholieke Univ Leuven, Dept Chem, LOMAC, B-3001 Louvain, Belgium
来源
SYNTHESIS-STUTTGART | 2011年 / 10期
关键词
2-aminoimidazoles; spiro compounds; tandem reaction; ring closure; silver; MICROWAVE-ASSISTED SYNTHESIS; DRAGMACIDIN-E SYNTHESIS; SPONGE LEUCETTA SP; IMIDAZOLE ALKALOIDS; MARINE SPONGE; CALCAREOUS SPONGE; OXAZOLE; CONSTRUCTION; CERATAMINE; PALAUAMINE;
D O I
10.1055/s-0030-1260012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper( I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA(2)-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2-iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.
引用
收藏
页码:1587 / 1594
页数:8
相关论文
共 58 条
  • [1] 2 IMIDAZOLE ALKALOIDS FROM A SPONGE
    AKEE, RK
    CARROLL, TR
    YOSHIDA, WY
    SCHEUER, PJ
    STOUT, TJ
    CLARDY, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1944 - 1946
  • [2] Synthesis of marine alkaloids from the oroidin family
    Arndt, Hans-Dieter
    Riedrich, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) : 4785 - 4788
  • [3] Synthesis and Antibiofilm Activity of a Second-Generation Reverse-Amide Oroidin Library: A Structure-Activity Relationship Study
    Ballard, T. Eric
    Richards, Justin J.
    Wolfe, Amanda L.
    Melander, Christian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) : 10745 - 10761
  • [4] Efficient Microwave-Assisted Synthesis of Secondary Alkylpropargylamines by Using A3-Coupling with Primary Aliphatic Amines
    Bariwal, Jitender B.
    Ermolat'ev, Denis S.
    Van der Eyeken, Erik V.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) : 3281 - 3284
  • [5] Natural guanidine derivatives
    Berlinck, RGS
    Kossuga, MH
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (04) : 516 - 550
  • [6] Natural guanidine derivatives
    Berlinck, RGS
    [J]. NATURAL PRODUCT REPORTS, 2002, 19 (05) : 617 - 649
  • [7] The chemistry and biology of organic guanidine derivatives
    Berlinck, Roberto G. S.
    Burtoloso, Antonio Carlos B.
    Kossuga, Miriam H.
    [J]. NATURAL PRODUCT REPORTS, 2008, 25 (05) : 919 - 954
  • [8] The chemistry and biology of organic guanidine derivatives
    Berlinck, Roberto G. S.
    Burtoloso, Antonio Carlos B.
    Trindade-Silva, Amaro E.
    Romminger, Stelamar
    Morais, Raquel P.
    Bandeira, Karin
    Mizuno, Carolina M.
    [J]. NATURAL PRODUCT REPORTS, 2010, 27 (12) : 1871 - 1907
  • [9] Revised structure of palau'amine
    Buchanan, Malcolm S.
    Carroll, Anthony R.
    Quinn, Ronald J.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (26) : 4573 - 4574
  • [10] Dragmacidins:: New protein phosphatase inhibitors from a southern Australian deep-water marine sponge, Spongosorites sp.
    Capon, RJ
    Rooney, F
    Murray, LM
    Collins, E
    Sim, ATR
    Rostas, JAP
    Butler, MS
    Carroll, AR
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05): : 660 - 662