Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds

被引:1082
作者
Orru, RVA [1 ]
de Greef, M [1 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem, NL-1081 HV Amsterdam, Netherlands
来源
SYNTHESIS-STUTTGART | 2003年 / 10期
关键词
heterocycles; multi-component reactions; combinatorial chemistry; parallel synthesis;
D O I
10.1055/s-2003-40507
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Following the increased interest from the pharmaceutical industry for the generation of diverse libraries of heterocyclic compounds, scientific efforts have become more and more focused on the development of novel multi-component procedures as a means of gaining rapid access to such compounds. Initially, the development of solid-phase procedures received considerable attention. However, current efforts are increasingly concerned with the development of solution-phase procedures. The latter will be the subject of discussion in this review, which aims to give an overview of the progress made in the past decade. After a general introduction, non-catalyzed, acid-catalyzed, and transition metal-catalyzed solution-phase multi-component procedures for the preparation of a wide range of heterocycles will be discussed. The last chapter discusses the role of cycloaddition reactions in the development of novel MCRs for the synthesis of heterocyclic compounds. In spite of their important role in the synthesis of heterocyclic compounds, MCRs involving isocyanides are not discussed in this review, since the topic has been exhaustively reviewed several times. 1 Introduction 2 Non-Catalyzed MCRs 3 Acid-Catalyzed MCRs 4 Transition Metal-Catalyzed or -Mediated MCRs 5 MCRs Involving Cycloaddition Reactions 6 Conclusions and Outlook.
引用
收藏
页码:1471 / 1499
页数:29
相关论文
共 174 条
  • [1] Novel catalytic and asymmetric process for aziridination mediated by sulfur ylides
    Aggarwal, VK
    Thompson, A
    Jones, RVH
    Standen, MCH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8368 - 8369
  • [2] Akiyama T, 2002, SYNLETT, P1898
  • [3] Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media
    Akiyama, T
    Takaya, J
    Kagoshima, H
    [J]. TETRAHEDRON LETTERS, 1999, 40 (44) : 7831 - 7834
  • [4] Indium triflate - An efficient catalyst for hetero Diels-Alder reactions
    Ali, T
    Chauhan, KK
    Frost, CG
    [J]. TETRAHEDRON LETTERS, 1999, 40 (30) : 5621 - 5624
  • [5] SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED CYCLIC ALPHA-AMINO-ACIDS STRUCTURALLY RELATED TO ACPD
    ALONSO, F
    MICO, I
    NAJERA, C
    SANSANO, JM
    YUS, M
    EZQUERRA, J
    YRURETAGOYENA, B
    GRACIA, I
    [J]. TETRAHEDRON, 1995, 51 (37) : 10259 - 10280
  • [6] A new multicomponent synthesis of 1,2,3,4-tetrahydroquinolines
    Annunziata, R
    Cinquini, M
    Cozzi, F
    Molteni, V
    Schupp, O
    [J]. TETRAHEDRON, 1997, 53 (28) : 9715 - 9726
  • [7] Annunziata R, 2002, EUR J ORG CHEM, V2002, P1184
  • [8] Yb(OTf)(3)-Catalyzed one-pot synthesis of beta-lactams from silyl ketene thioacetals by a two- or a three-component reaction
    Annunziata, R
    Cinquini, M
    Cozzi, F
    Molteni, V
    Schupp, O
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8293 - 8296
  • [9] Stereoselective one-pot synthesis of beta-lactams by Lewis acid promoted condensation of silylketene thioacetals with imines
    Annunziata, R
    Cinquini, M
    Cozzi, F
    Molteni, V
    Schupp, O
    [J]. TETRAHEDRON, 1996, 52 (07) : 2573 - 2582
  • [10] [Anonymous], 1890, BER DTSCH CHEM GES, DOI DOI 10.1002/CBER.189002301243