Recent synthetic strategies for N-arylation of pyrrolidines: a potential template for biologically active molecules

被引:0
作者
Mubashra, Saeeda [1 ]
Rafiq, Ayesha [1 ]
Aslam, Sana [2 ]
Rasool, Nasir [1 ]
Ahmad, Matloob [1 ]
机构
[1] Govt Coll Univ Faisalabad, Dept Chem, Faisalabad 38000, Pakistan
[2] Govt Coll Women Univ Faisalabad, Dept Chem, Faisalabad 38000, Pakistan
关键词
Pyrrolidine; Pyrrolidine-2-one; Synthesis; N-Arylation; (HETERO)ARYL CHLORIDES; ARYL AMINATION; AMINES; EFFICIENT; ALKALOIDS; CATALYST; ULLMANN; LIGAND; INHIBITORS; DISCOVERY;
D O I
10.1007/s11030-024-10924-7
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The chemistry of nitrogen-containing heterocyclic compounds has been a multifaceted area of research for an extended period due to their varied therapeutic and biological significance. N-Aryl pyrrolidine formed by condensation of aryl group with nitrogen atom of pyrrolidine is present in a wide array of compounds. Various significant activities shown by N-arylated pyrrolidine include anti-Alzheimer, antihypoxic, anticancer, plant activator, analgesic effect, and hepatitis C inhibitor. This review summarizes different synthetic approaches, e.g., transition-metal catalyzed and transition-metal-free synthesis, decarboxylation reaction, reductive amination, nucleophilic cyclization, Ullmann-Goldberg amidation, Buchwald-Hartwig reaction, Chan-Evans-Lam coupling, addition to benzyne, multistep reaction, green synthesis, rearrangement reaction, and multicomponent reaction, to afford the derivatives of N-aryl pyrrolidine. It encompasses synthetic strategies documented from 2015 to 2023. {GRAPHIACAL ABSTRACT}
引用
收藏
页码:1851 / 1893
页数:43
相关论文
共 111 条
  • [1] Cu-NHC Complex for Chan-Evans-Lam Cross-Coupling Reactions of N-Heterocyclic Compounds and Arylboronic Acids
    Adhikari, Bhupendra
    Teimouri, Mohsen
    Akin, James W.
    Raju, Selvam
    Stokes, Sean L.
    Emerson, Joseph P.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [2] Molecular docking and antiviral activity of N-substituted benzyl/phenyl-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin2(4H)-yl) acetamides
    Ahmad, Matloob
    Aslam, Sana
    Rizvi, Syed Umar Farooq
    Muddassar, Muhammad
    Ashfaq, Usman Ali
    Montero, Catherine
    Ollinger, Olivia
    Detorio, Mervi
    Gardiner, John M.
    Schinazi, Raymond F.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (06) : 1348 - 1351
  • [3] Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs). Part I
    Aikawa, Katsuji
    Miyawaki, Toshio
    Hitaka, Takenori
    Imai, Yumi N.
    Hara, Takahito
    Miyazaki, Junichi
    Yamaoka, Masuo
    Kusaka, Masami
    Kanzaki, Naoyuki
    Tasaka, Akihiro
    Shiraishi, Mitsuru
    Yamamoto, Satoshi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (10) : 2568 - 2578
  • [4] Recent Advances in Reductive Amination Catalysis and Its Applications
    Alinezhad, Heshmatollah
    Yavari, Hossein
    Salehian, Fatemeh
    [J]. CURRENT ORGANIC CHEMISTRY, 2015, 19 (11) : 1021 - 1049
  • [5] Aslam S, 2014, ARCH PHARM RES, V37, P1380, DOI 10.1007/s12272-013-0200-9
  • [6] Therapeutic potential of pyrrole and pyrrolidine analogs: an update
    Basha, N. Jeelan
    Basavarajaiah, S. M.
    Shyamsunder, K.
    [J]. MOLECULAR DIVERSITY, 2022, 26 (05) : 2915 - 2937
  • [7] Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues
    Baudelet, Davy
    Daich, Adam
    Rigo, Benoit
    Lipka, Emmanuelle
    Gautret, Philippe
    Homerin, Germain
    Claverie, Christelle
    Rousseau, Jolanta
    Abuhaie, Cristina-Maria
    Ghinet, Alina
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (14): : 2226 - 2244
  • [8] Synthetic Studies of Alkaloids Containing Pyrrolidine and Piperidine Structural Motifs
    Bhat, Chinmay
    [J]. CHEMISTRYOPEN, 2015, 4 (02): : 192 - 196
  • [9] Recent advances in the synthesis of naturally occurring pyrrolidines, pyrrolizidines and indolizidine alkaloids using proline as a unique chiral synthon
    Bhat, Chinmay
    Tilve, Santosh G.
    [J]. RSC ADVANCES, 2014, 4 (11) : 5405 - 5452
  • [10] N,N′-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines
    Bhunia, Subhajit
    Kumar, S. Vijay
    Ma, Dawei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12603 - 12612