Synthesis of coumarin dimers by a microwave-assisted double multicomponent reaction

被引：0
作者：
Ramiro, Jose Luis [1 ]
Marcos, Carlos F. [1 ]
Neo, Ana G. [1 ]
机构：
[1] Univ Extremadura, Lab Bioorgan Chem & Membrane Biophys LOBO, Caceres 10003, Spain
来源：
SUSTAINABLE CHEMISTRY AND PHARMACY | 2024年 / 42卷
关键词：
Microwave; Coumarin; Peptidomimetic; Enol-Ugi; PERSPECTIVE; ACCESS;
D O I：
10.1016/j.scp.2024.101792
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthesis of coumarin dimers highly functionalized was developed using a double enol-Ugi reaction. The use of microwave irradiation permits the construction of this complex coumarin derivatives in only 5 min. This is the first report of a double enol-Ugi condensation using dialdehydes and diamines affording peptidomimetic coumarin dimers with different linkers and substituents. This methodology permits to obtain molecular diversity and complexity by a multicomponent protocol under microwave activation. The described double enol-Ugi reactions demonstrate excellent atom economy and favourable waste prevention metrics.
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页数：8
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共 45 条
  • [1] Materials Functionalization with Multicomponent Reactions: State of the Art
    Afshari, Ronak
    Shaabani, Ahmad
    [J]. ACS COMBINATORIAL SCIENCE, 2018, 20 (09) : 499 - 528
  • [2] Multicomponent molecular memory
    Arcadia, Christopher E.
    Kennedy, Eamonn
    Geiser, Joseph
    Dombroski, Amanda
    Oakley, Kady
    Chen, Shui-Ling
    Sprague, Leonard
    Ozmen, Mustafa
    Sello, Jason
    Weber, Peter M.
    Reda, Sherief
    Rose, Christopher
    Kim, Eunsuk
    Rubenstein, Brenda M.
    Rosenstein, Jacob K.
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)
  • [3] Recent advances and therapeutic journey of coumarins: current status and perspectives
    Barot, Kuldipsinh P.
    Jain, Shailesh V.
    Kremer, Laurent
    Singh, Shubhra
    Ghate, Manjunath D.
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (07) : 2771 - 2798
  • [4] Synthesis of Chromeno[3,4-b]piperazines by an Enol-Ugi/Reduction/Cyclization Sequence
    Bornadiego, Ana
    Neo, Ana G.
    Marcos, Carlos F.
    [J]. MOLECULES, 2021, 26 (05):
  • [5] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?
    Brow, Dean G.
    Bostrom, Jonas
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) : 4443 - 4458
  • [6] Key Green Chemistry research areas from a pharmaceutical manufacturers' perspective revisited
    Bryan, Marian C.
    Dunn, Peter J.
    Entwistle, David
    Gallou, Fabrice
    Koenig, Stefan G.
    Hayler, John D.
    Hickey, Matthew R.
    Hughes, Shaun
    Kopach, Michael E.
    Moine, Gerard
    Richardson, Paul
    Roschangar, Frank
    Steven, Alan
    Weiberth, Franz J.
    [J]. GREEN CHEMISTRY, 2018, 20 (22) : 5082 - 5103
  • [7] Enols as Feasible Acid Components in the Ugi Condensation
    Castellano, Teresa G.
    Neo, Ana G.
    Marcaccini, Stefano
    Marcos, Carlos F.
    [J]. ORGANIC LETTERS, 2012, 14 (24) : 6218 - 6221
  • [8] GreenMedChem: the challenge in the next decade toward eco-friendly compounds and processes in drug design
    Castiello, Carola
    Junghanns, Pierre
    Mergel, Annika
    Jacob, Claus
    Ducho, Christian
    Valente, Sergio
    Rotili, Dante
    Fioravanti, Rossella
    Zwergel, Clemens
    Mai, Antonello
    [J]. GREEN CHEMISTRY, 2023, 25 (06) : 2109 - 2169
  • [9] The Ugi three-component reaction and its variants
    Cesar Flores-Reyes, Julio
    Islas-Jacome, Alejandro
    Gonzalez-Zamora, Eduardo
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (19) : 5460 - 5515
  • [10] Cioc R., 2022, Green Chemistry in Drug Discovery: from Academia to Industry, P237
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