1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles

被引:195
作者
Groenendaal, Bas [1 ]
Ruijter, Eelco [1 ]
Orru, Romano V. A. [1 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, NL-1081 HV Amsterdam, Netherlands
关键词
D O I
10.1039/b809206k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1-Azadienes are versatile building blocks for the efficient construction of various N-heterocycles. Depending on the substitution pattern and reaction partner, they may participate in a range of different reactions. An overview of recent methods for the generation of 1-azadienes is presented, as well as their application in cycloaddition, electrocyclization, and multicomponent reactions. Considering the broad range of reactivities and resulting heterocyclic scaffold structures, 1-azadienes are very useful reactive intermediates for the development of modular reaction sequences in diversity-oriented synthesis.
引用
收藏
页码:5474 / 5489
页数:16
相关论文
共 80 条
  • [31] A multicomponent synthesis of triazinane diones
    Groenendaal, Bas
    Vugts, Danielle J.
    Schmitz, Rob F.
    de Kanter, Frans J. J.
    Ruijter, Eelco
    Groen, Marinus B.
    Orru, Romano V. A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) : 719 - 722
  • [32] The principle of complementarity:: chemical versus biological space
    Haggarty, SJ
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2005, 9 (03) : 296 - 303
  • [33] Highly enantioselective azadiene Diels-Alder reactions catalyzed by chiral N-heterocyclic carbenes
    He, Ming
    Struble, Justin R.
    Bode, Jeffrey W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) : 8418 - 8420
  • [34] Henkel T, 1999, ANGEW CHEM INT EDIT, V38, P643, DOI 10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO
  • [35] 2-G
  • [36] Intramolecular Diels-Alder reactions of α,β-unsaturated oxime ethers as 1-azadienes:: synthesis of [c]-fused pyridines
    Hurst, Timothy E.
    Miles, Timothy J.
    Moody, Christopher J.
    [J]. TETRAHEDRON, 2008, 64 (05) : 874 - 882
  • [37] Recent advances in synthetic applications of azadienes
    Jayakumar, S
    Ishar, MPS
    Mahajan, MP
    [J]. TETRAHEDRON, 2002, 58 (03) : 379 - 471
  • [38] Biology-inspired synthesis of compound libraries
    Kaiser, M.
    Wetzel, S.
    Kumar, K.
    Waldmann, H.
    [J]. CELLULAR AND MOLECULAR LIFE SCIENCES, 2008, 65 (7-8) : 1186 - 1201
  • [39] Novel one pot synthesis of polysubstituted pyrazolo[1,5-a]- and imidazo[1,2-a]pyrimidines
    Kiselyov, AS
    Smith, L
    [J]. TETRAHEDRON LETTERS, 2006, 47 (15) : 2611 - 2614
  • [40] One-pot synthesis of polysubstituted pyrimidines
    Kiselyov, AS
    [J]. TETRAHEDRON LETTERS, 2005, 46 (10) : 1663 - 1665