Synthesis of polyheterocycles via multicomponent reactions

被引:212
作者
Ibarra, Ilich A. [1 ]
Islas-Jacome, Alejandro [2 ]
Gonzalez-Zamora, Eduardo [2 ]
机构
[1] Univ Nacl Autonoma Mexico, Inst Invest Mat, Lab Fisicoquim & Reactividad Superficies LAFReS, Circuito Exterior S-N, Mexico City 04510, DF, Mexico
[2] Univ Autonoma Metropolitana Iztapalapa, Dept Quim, San Rafael Atlixco 186, Mexico City 09340, DF, Mexico
关键词
DIVERSE HETEROCYCLIC SCAFFOLDS; NUEVAMINE AZA-ANALOGS; ONE-POT SYNTHESIS; NITROGEN-HETEROCYCLES; RADICAL CYCLIZATION; ORIENTED SYNTHESIS; 3-COMPONENT CONDENSATION; MOLECULAR COMPLEXITY; MEDICINAL CHEMISTRY; CYANOACETIC ACID;
D O I
10.1039/c7ob02305g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polyheterocycles are one of the most desired synthetic targets due to their numerous and valuable applications in various fields. Multicomponent reactions (MCRs) are highly convergent one-pot processes, in which three or more reagents are combined sequentially to construct complex products, with almost all the atoms coming from the starting reagents. In this context, the syntheses of 'heterocycles' via MCR-based processes have been reviewed a number of times. However, there is not a single review (recent or otherwise) covering the synthesis of 'polyheterocycles' via a direct MCR or via a one-pot process involving MCRs coupled to further cyclizations (via ionic, metal-catalyzed, pericyclic, or free-radical-mediated cyclizations). This issue is consequently the main topic of the present review, which considers work from the last decade. The work is categorized according to the key processes involved in the syntheses of polyheterocycles, aiming to give readers an easy understanding of this MCR-based chemistry and to provide insights for further investigations. The reaction mechanisms providing novel elements to these MCR-based methods for the synthesis of polyheterocycles are also discussed.
引用
收藏
页码:1402 / 1418
页数:17
相关论文
共 109 条
  • [51] Synthesis of unsymmetrical bis-heterocycles containing the imidazo [2,1-b]thiazole framework and their benzo[d]fused analogues by an acid-free Groebke-Blackburn-Bienayme reaction
    Kishore, Kranthi G.
    Islas-Jacome, Alejandro
    Renteria-Gomez, Angel
    Conejo, Alain S.
    Basavanag, Unnamatla M. V.
    Wrobel, Kazimierz
    Gamez-Montano, Rocio
    [J]. TETRAHEDRON LETTERS, 2016, 57 (31) : 3556 - 3560
  • [52] Insertion of Isocyanides into N-Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds
    Kishore, Kranti G.
    Ghashghaei, Ouldouz
    Estarellas, Carolina
    Mar Mestre, M.
    Monturiol, Cristina
    Kielland, Nicola
    Kelly, John M.
    Fortes Francisco, Amanda
    Jayawardhana, Shiromani
    Munoz-Torrero, Diego
    Perez, Belen
    Javier Luque, F.
    Gamez-Montano, Rocio
    Lavilla, Rodolfo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) : 8994 - 8998
  • [53] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO
  • [54] 2-X
  • [55] Multicomponent Syntheses of Fluorophores Initiated by Metal Catalysis
    Levi, Lucilla
    Mueller, Thomas J. J.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 2907 - 2918
  • [56] Multicomponent syntheses of functional chromophores
    Levi, Lucilla
    Mueller, Thomas J. J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) : 2825 - 2846
  • [57] Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation
    Li, Zhenghua
    Zhao, Yaping
    Tian, Guilong
    He, Yi
    Song, Gonghua
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    [J]. RSC ADVANCES, 2016, 6 (105): : 103601 - 103605
  • [58] A domino Ugi/Michael approach for the synthesis of α,β-unsaturated γ-lactams
    Li, Zhenghua
    Kumar, Amit
    Peshkov, Anatoly
    Van der Eycken, Erik V.
    [J]. TETRAHEDRON LETTERS, 2016, 57 (07) : 754 - 756
  • [59] Lipinski Christopher A, 2004, Drug Discov Today Technol, V1, P337, DOI 10.1016/j.ddtec.2004.11.007
  • [60] Efficient and Diverse Synthesis of Indole Derivatives
    Liu, Haixia
    Doemling, Alexander
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) : 6895 - 6898