Gold-Catalyzed Post-Ugi Cascade Transformation for the Synthesis of 2-Pyridones

被引：15
作者：
Du, Xiaochen [1 ]
Yu, Jiafeng [1 ]
Gong, Jing [1 ]
Zaman, Manzoor [1 ]
Pereshivko, Olga P. [1 ]
Peshkov, Vsevolod A. [1 ,2 ,3 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Dushu Lake Campus, Suzhou 215123, Peoples R China
[2] Nazarbayev Univ, Sch Sci & Technol, Dept Chem, 53 Kabanbay Batyr Ave,Block 7, Astana 010000, Kazakhstan
[3] Nazarbayev Univ, EREC, Astana, Kazakhstan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 14期
基金：
中国国家自然科学基金;
关键词：
Cascade transformations; Gold catalysis; Multicomponent reactions; 2-Pyridones; Ugi reaction; INTRAMOLECULAR HYDROARYLATION; ONE-POT; REGIOSELECTIVE SYNTHESIS; CONSTRUCTION; ALKYNES; CYCLOISOMERIZATIONS; PYRROLOPYRIDINONES; HETEROCYCLES; SELECTIVITY; ARENES;
D O I：
10.1002/ejoc.201900027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A gold-catalyzed post-Ugi cascade transformation for the synthesis of 2-pyridones is described. The process involves furan-alkyne cyclization followed by furan ring-opening and cleavage of the isocyanide-originated fragment. The initially formed cis double bond can isomerize into a more stable trans double bond upon prolonged exposure to a strong Bronsted acid. Thus, the overall strategy provides a viable access towards two types of 2-pyridones.
引用
收藏
页码：2502 / 2507
页数：6
相关论文
共 75 条
  • [41] Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2:: The role of platinum carbenes as intermediates
    Martín-Matute, B
    Nevado, C
    Cárdenas, DJ
    Echavarren, AM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) : 5757 - 5766
  • [42] Modha S. G., 2012, ANGEW CHEM, V124, P9710
  • [43] Gold(I) and platinum(II) switch: a post-Ugi intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones
    Modha, Sachin G.
    Kumar, Amit
    Vachhani, Dipak D.
    Sharma, Sunil K.
    Parmar, Virinder S.
    Van der Eycken, Erik V.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (88) : 10916 - 10918
  • [44] A Diversity-Oriented Approach to Spiroindolines: Post-Ugi Gold-Catalyzed Diastereoselective Domino Cyclization
    Modha, Sachin G.
    Kumar, Amit
    Vachhani, Dipak D.
    Jacobs, Jeroen
    Sharma, Sunil K.
    Parmar, Virinder S.
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9572 - 9575
  • [45] Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles
    Murlykina, Maryna V.
    Morozova, Alisa D.
    Zviagin, Ievgen M.
    Sakhno, Yana I.
    Desenko, Sergey M.
    Chebanov, Valentyn A.
    [J]. FRONTIERS IN CHEMISTRY, 2018, 6
  • [46] Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity
    Nechaev, Anton A.
    Van Hecke, Kristof
    Zaman, Manzoor
    Kashtanov, Stepan
    Ungur, Liviu
    Pereshivko, Olga P.
    Peshkov, Vsevolod A.
    Van der Eycken, Erik V.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) : 8170 - 8182
  • [47] Nicolaou K., 2006, Angew. Chem, V118, P7292, DOI DOI 10.1002/ANGE.200601872
  • [48] Cascade reactions in total synthesis
    Nicolaou, K. C.
    Edmonds, David J.
    Bulger, Paul G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) : 7134 - 7186
  • [49] Gold-Catalyzed Cascade Reactions of Alkynes for Construction of Polycyclic Compounds
    Ohno, Hiroaki
    [J]. ISRAEL JOURNAL OF CHEMISTRY, 2013, 53 (11-12) : 869 - 882
  • [50] Stereocontrolled Domino Reactions
    Pellissier, Helene
    [J]. CHEMICAL REVIEWS, 2013, 113 (01) : 442 - 524
12345678