Propagative isatin in organic synthesis of spirooxindoles through catalysis

被引:20
作者
Asif, Mohd [1 ]
Azaz, Tazeen [2 ]
Tiwari, Bhoopendra [2 ]
Nasibullah, Malik [1 ,3 ]
机构
[1] Integral Univ, Dept Chem, Res Lab, Lucknow 226026, UP, India
[2] SGPGIMS Campus, Ctr Biomed Res, Dept Biol & Synthet Chem, Raebareli Rd, Lucknow 226014, UP, India
[3] Integral Univ, Dept Chem, Lucknow, UP, India
关键词
Multi-component reactions; Catalysis; Spirooxindole-scaffolds and synthesis; DERIVATIVES; EFFICIENT; OXINDOLE; GREEN; ACCESS;
D O I
10.1016/j.tet.2023.133308
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxindole (indoline-2, 3-dione) has been utilized to a great extent in heterocyclic scaffold syntheses as a futuristic medication and is considered a prominent building block used in organic synthesis. Herein, oxindole promotes multi-component reactions w.r.t. initiative candidates for the formation of spiroox-indole scaffolds. This review reflects the advances of oxindole in organic synthesis as a selected starting material in the formation of spirooxindoles from 2015 to 2022. Remarkable spirooxindoles have isolated distinct genus (plants and animals), and their origins have significant recreation opportunities in me-dicinal chemistry. Spiro-skeleton compounds have cyclic structures which are fused on a central carbon (sp3 hybridized), obtaining interesting conformational features to favour anti-proliferation evaluation. The obvious reaction mechanisms involve the plausible reactivity of the reactants, the catalyst interac-tion, and the cyclization to produce spirooxindole derivatives. (c) 2023 Elsevier Ltd. All rights reserved.
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页数:22
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共 74 条
  • [1] Chameleon-Like Activating Nature of the Spirooxindole Group in Donor-Acceptor Cyclopropanes
    Akaev, Audrey A.
    Melnikov, Mikhail Ya.
    Budynina, Ekaterina M.
    [J]. ORGANIC LETTERS, 2019, 21 (23) : 9795 - 9799
  • [2] Antitumor properties of certain spirooxindoles towards hepatocellular carcinoma endowed with antioxidant activity
    Al-Rashood, Sara T.
    Hamed, Ahmed R.
    Hassan, Ghada S.
    Alkahtani, Hamad M.
    Almehizia, Abdulrahman A.
    Alharbi, Amal
    Al-Sanea, Mohammad M.
    Eldehna, Wagdy M.
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2020, 35 (01) : 831 - 839
  • [3] Broad spectrum antimicrobial activity of dispirooxindolopyrrolidine fused acenaphthenone heterocyclic hybrid against healthcare associated microbial pathogens (HAMPs)
    Almansour, Abdulrahman I.
    Arumugam, Natarajan
    Kumar, Raju Suresh
    Raju, Rajesh
    Ponmurugan, Karuppiah
    Al-Dhabi, Naif Abdullah
    Premnath, Dhanaraj
    [J]. JOURNAL OF INFECTION AND PUBLIC HEALTH, 2020, 13 (12) : 2001 - 2008
  • [4] Potential role of lycopene in targeting proprotein convertase subtilisin/kexin type-9 to combat hypercholesterolemia
    Alvi, Sahir Sultan
    Ansari, Irfan A.
    Khan, Imran
    Iqbal, Johar
    Khan, M. Salman
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 2017, 108 : 394 - 403
  • [5] Regio- and diastereoselective synthesis of anticancer spirooxindoles derived from tryptophan and histidine via three-component 1,3-dipolar cycloadditions in an ionic liquid
    Arumugam, Natarajan
    Almansour, Abdulrahman I.
    Kumar, Raju Suresh
    Periasamy, Vaiyapuri Subbarayan
    Athinarayanan, Jegan
    Alshatwi, Ali A.
    Govindasami, Periyasami
    Altaf, Mohammad
    Carlos Menendez, J.
    [J]. TETRAHEDRON, 2018, 74 (38) : 5358 - 5366
  • [6] Bronsted acidic ionic liquids: Green, efficient and reusable catalyst for synthesis of fluorinated Spiro [indole-thiazinones/thiazolidinones] as antihistamic agents
    Arya, Kapil
    Rawat, Diwan Singh
    Dandia, Anshu
    Sasai, Hiroaki
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2012, 137 : 117 - 122
  • [7] Combining C-H functionalisation and flow photochemical heterocyclic metamorphosis (FP-HM) for the synthesis of benzo[1,3]oxazepines
    Babra, Jasraj S.
    Russell, Andrew T.
    Smith, Christopher D.
    Zhang, Yuxiong
    [J]. TETRAHEDRON, 2018, 74 (38) : 5351 - 5357
  • [8] Preyssler-based nanocomposite as a magnetic photocatalyst: synthesis, characterisation and its photocatalytic activity for decolourisation of rhodamine B
    Bamoharram, Fatemeh F.
    Mozhdehi, AmirMohammad
    Radfar, Azadeh
    Shaker, Mohammad
    Mallaeke, Hassan
    Sharifi, Amir Hossein
    [J]. MICRO & NANO LETTERS, 2018, 13 (12) : 1657 - 1661
  • [9] Synthesis and anti-Cancer Activity of a New Hybrid Based Spirooxindole-Pyrrolidine -Thiochromene Scaffolds via [3+2] Cycloaddition Reaction: Computational Investigation
    Barakat, Assem
    Haukka, Matti
    Soliman, Saied M.
    Al-Majid, Abdullah Mohammed
    Ali, M.
    Islam, Mohammad Shahidul
    Karami, Abdulnasser Mahmoud
    Ul-Haq, Zaheer
    Domingo, Luis R.
    [J]. POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (03) : 2302 - 2320
  • [10] Substituted spirooxindole derivatives as potent anticancer agents through inhibition of phosphodiesterase 1
    Barakat, Assem
    Islam, Mohammad Shahidul
    Ghawas, Hussien Mansur
    Al-Majid, Abdullah Mohammed
    El-Senduny, Fardous F.
    Badria, Farid A.
    Elshaier, Yaseen A. M. M.
    Ghabbour, Hazem A.
    [J]. RSC ADVANCES, 2018, 8 (26) : 14335 - 14346