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
  • [1] Toward the library generation of natural product-like polycyclic derivatives by stereocontrolled diversity-oriented synthesis
    Arya, R
    Quevillon, S
    Joseph, R
    Wei, CQ
    Gan, Z
    Parisien, M
    Sesmilo, E
    Reddy, RT
    Chen, ZX
    Durieux, R
    Laforce, D
    Campeau, LC
    Khadem, S
    Couve-Bonnaire, S
    Kumar, R
    Sharma, U
    Leek, DM
    Daroszewska, M
    Barnes, ML
    [J]. PURE AND APPLIED CHEMISTRY, 2005, 77 (01) : 163 - 178
  • [2] Formal alkyne insertion into alkoxycarbene complexes:: Simple access to enantiopure group 6 alkynyl(alkoxy)carbene complexes
    Barluenga, J
    de la Rúa, RB
    de Sáa, D
    Ballesteros, A
    Tomás, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) : 4981 - 4983
  • [3] A facile and diastereoselective access to substituted cyclopentanones from Fischer alkenyl carbene complexes and 1-amino-1-azadienes
    Barluenga, J
    Ballesteros, A
    Santamaría, J
    Tomás, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 : 363 - 368
  • [4] ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL 1-AZADIENES
    BEAUDEGNIES, R
    GHOSEZ, L
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (04) : 557 - 560
  • [5] Diels-Alder reactions of 1-azadienes
    Behforouz, M
    Ahmadian, M
    [J]. TETRAHEDRON, 2000, 56 (30) : 5259 - 5288
  • [6] Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides
    Berry, CR
    Hsung, RP
    [J]. TETRAHEDRON, 2004, 60 (35) : 7629 - 7636
  • [7] Libraries from natural product-like scaffolds
    Boldi, AM
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (03) : 281 - 286
  • [8] Natural product guided compound library development
    Breinbauer, R
    Manger, M
    Scheck, M
    Waldmann, H
    [J]. CURRENT MEDICINAL CHEMISTRY, 2002, 9 (23) : 2129 - 2145
  • [9] Breinbauer R, 2002, ANGEW CHEM INT EDIT, V41, P2879
  • [10] Generating diverse skeletons of small molecules combinatorially
    Burke, MD
    Berger, EM
    Schreiber, SL
    [J]. SCIENCE, 2003, 302 (5645) : 613 - 618