A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas

被引:65
|
作者
Fritz, Jonathan A. [1 ]
Nakhla, Josephine S. [1 ]
Wolfe, John P. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ol060707b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one products with generation of two bonds and up to two stereocenters when treated with aryl bromides and catalytic amounts of Pd-2(dba)(3)/Xantphos in the presence of (NaOBu)-Bu-t.
引用
收藏
页码:2531 / 2534
页数:4
相关论文
共 50 条
  • [31] Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones
    Gazieva G.A.
    Lozhkin P.V.
    Kravchenko A.N.
    Lysenko K.A.
    Kolotyrkina N.G.
    Makhova N.N.
    Chemistry of Heterocyclic Compounds, 2007, 43 (8) : 981 - 988
  • [32] Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones
    Gazieva, G. A.
    Lozhkin, P. V.
    Kravchenko, A. N.
    Lysenko, K. A.
    Kolotyrkina, N. G.
    Makhova, N. N.
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (08): : 1159 - 1166
  • [33] Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions
    Peterson, Luke J.
    Luo, Jingyi
    Wolfe, John P.
    ORGANIC LETTERS, 2017, 19 (11) : 2817 - 2820
  • [34] A concise asymmetric synthesis of cis-2,6-disubstituted N-aryl piperazines via Pd-catalyzed carboamination reactions
    Nakhla, Josephine S.
    Wolfe, John P.
    ORGANIC LETTERS, 2007, 9 (17) : 3279 - 3282
  • [35] Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
    La-Venia, Agustina
    Medran, Noelia S.
    Krchnak, Viktor
    Testero, Sebastian A.
    ACS COMBINATORIAL SCIENCE, 2016, 18 (08) : 482 - 489
  • [36] A convenient synthesis of 3-amino-4-imino(thioxo)-imidazolidin-2-ones
    Kurz, T
    Widyan, K
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7049 - 7051
  • [37] Pd-Catalyzed Carboamination of Oxazolidin-2-ones: A Stereoselective Route to trans-2,5-Disubstituted Pyrrolidines
    Lemen, Georgia S.
    Wolfe, John P.
    ORGANIC LETTERS, 2010, 12 (10) : 2322 - 2325
  • [38] Synthesis of Polycyclic Nitrogen Heterocycles via Cascade Pd-Catalyzed Alkene Carboamination/Diels-Alder Reactions
    White, Derick R.
    Wolfe, John P.
    ORGANIC LETTERS, 2015, 17 (10) : 2378 - 2381
  • [39] Synthesis of Fluorine-Containing Imidazolidin-2-Ones, Glycolurils, and Hydantoins Based on Perfluorodiacetyl and Ureas*
    L. V. Saloutina
    A. Ya. Zapevalov
    P. A. Slepukhin
    M. I. Kodess
    V. I. Saloutin
    O. N. Chupakhin
    Chemistry of Heterocyclic Compounds, 2014, 50 : 958 - 966
  • [40] Lewis acid-catalyzed stereospecific ring expansion of aziridine-2carboxylates to imidazolidin-2-ones
    Kim, MS
    Kim, YW
    Hahm, HS
    Jang, JW
    Lee, WK
    Ha, HJ
    CHEMICAL COMMUNICATIONS, 2005, (24) : 3062 - 3064