The Application of Multicomponent Ugi and Passerini Reactions for the One-Pot Synthesis of Pyrrolones and Butenolides

被引:19
|
作者
Nechaev, Anton A. [1 ]
Peshkov, Anatoly A. [1 ]
Peshkov, Vsevolod A. [2 ]
Van der Eycken, Erik V. [1 ]
机构
[1] Univ Leuven, Dept Chem, LOMAC, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium
[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Dushu Lake Campus, Suzhou 215123, Peoples R China
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 14期
基金
比利时弗兰德研究基金会;
关键词
Ugi reaction; Passerini reaction; propiolic acid; ethyl glyoxylate; pyrrolone; butenolide; BETA-LACTAMS; COMBINATORIAL SYNTHESIS; FACILE SYNTHESIS; ISOCYANIDES; TRANSFORMATIONS; HETEROCYCLES; ANALOGS; ACCESS; ROUTE;
D O I
10.1055/s-0035-1561422
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new protocol for the one-pot synthesis of pyrrolones and butenolides involving an isocyanide-based multicomponent reaction (Ugi or Passerini) followed by a triethylamine-promoted cycloisomerization is described.
引用
收藏
页码:2280 / 2286
页数:7
相关论文
共 50 条
  • [31] Versatile synthesis of polysaccharide hydrogels using the Passerini and Ugi multicomponent condensations
    de Nooy, AEJ
    Masci, G
    Crescenzi, V
    [J]. MACROMOLECULES, 1999, 32 (04) : 1318 - 1320
  • [32] One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives
    Zheng, Hui
    Mei, Yi-Jia
    Du, Kui
    Cao, Xian-Ting
    Zhang, Peng-Fei
    [J]. MOLECULES, 2013, 18 (11): : 13425 - 13433
  • [33] Triphenylphosphine Catalyzed, One-Pot, Multicomponent Synthesis of Spirooxindoles
    Riyaz, Syed
    Naidu, A.
    Dubey, Pramod K.
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (02) : 101 - 105
  • [34] Ammonia-Promoted One-Pot Tetrazolopiperidinone Synthesis by Ugi Reaction
    Patil, Pravin
    Kurpiewska, Katarzyna
    Kalinowska-Tluscik, Justyna
    Domling, Alexander
    [J]. ACS COMBINATORIAL SCIENCE, 2017, 19 (05) : 343 - 350
  • [35] One-pot synthesis of -lactams by the Ugi and Michael addition cascade reaction
    Gao, Xing
    Shan, Chunhui
    Chen, Zhihao
    Liu, Yan
    Zhao, Xia
    Zhang, Ao
    Yu, Peng
    Galons, Herve
    Lan, Yu
    Lu, Kui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 6096 - 6105
  • [36] O-Silylative Passerini Reaction: A New One-Pot Synthesis of α-Siloxyamides
    Soeta, Takahiro
    Kojima, Yuuki
    Ukaji, Yutaka
    Inomata, Katsuhiko
    [J]. ORGANIC LETTERS, 2010, 12 (19) : 4341 - 4343
  • [37] One-pot synthesis of quinoline-fused [1,4]thiazepines via the tandem Ugi/post-Ugi reactions
    Ghandi, Mehdi
    Efteghar, Irene
    Abbasi, Alireza
    [J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (02) : 325 - 332
  • [38] One-pot synthesis of quinoline-fused [1,4]thiazepines via the tandem Ugi/post-Ugi reactions
    Mehdi Ghandi
    Irene Efteghar
    Alireza Abbasi
    [J]. Journal of the Iranian Chemical Society, 2019, 16 : 325 - 332
  • [39] One-pot enzymatic desymmetrization and Ugi MCR
    Fryszkowska, A
    Frelek, J
    Ostaszewski, R
    [J]. TETRAHEDRON, 2005, 61 (25) : 6064 - 6072
  • [40] A new modification of the Passerini reaction: a one-pot synthesis of α-acyloxyamides via sequential Kornblum cocidation/Passerini reaction
    Adib, Mehdi
    Sheikhi, Ehsan
    Azimzadeh, Marjan
    [J]. TETRAHEDRON LETTERS, 2015, 56 (15) : 1933 - 1936