Decarboxylative 1,3-dipolar cycloadditions of <sc>l</sc>-proline

被引：3
作者：
Doraghi, Fatemeh [1 ]
Serajian, Azam [2 ]
Karimian, Somaye [3 ]
Ghanbarlou, Mehdi [1 ]
Moradkhani, Fatemeh [1 ]
Larijani, Bagher [1 ]
Mahdavi, Mohammad [1 ]
机构：
[1] Univ Tehran Med Sci, Endocrinol & Metab Clin Sci Inst, Endocrinol & Metab Res Ctr, Tehran, Iran
[2] Inst Adv Studies Basic Sci IASBS, Dept Chem, Zanjan, Iran
[3] Shiraz Univ Med Sci, Med & Nat Prod Chem Res Ctr, Shiraz, Iran
来源：
RSC ADVANCES | 2024年 / 14卷 / 12期
关键词：
NONSTABILIZED AZOMETHINE YLIDES; BAYLIS-HILLMAN REACTION; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; OXINDOLE DERIVATIVES; DIASTEREOSELECTIVE SYNTHESIS; SPIROOXINDOLE DERIVATIVES; MOLECULAR DOCKING; FACILE SYNTHESIS;
D O I：
10.1039/d3ra08160e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1,3-Dipolar cycloaddition is one of the important chemical reactions between a 1,3-dipole and a dipolarophile to construct a five-membered heterocyclic compound. As an available alpha-amino acid reactant, l-proline is extensively used in 1,3-dipolar cycloaddition reactions. A diverse spectrum of bioactive spiro and fused N-heterocycles is obtained through this synthetic approach. In this review, we have described the use of l-proline in the synthesis of various spiro- and fused heterocyclic scaffolds.
引用
收藏
页码：8481 / 8501
页数：21
相关论文
共 109 条
  • [1] Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (83) : 12434 - 12446
  • [2] Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using l-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst
    Akhavan, Malihe
    Bekhradnia, Ahmadreza
    [J]. RSC ADVANCES, 2021, 11 (24) : 14755 - 14768
  • [3] Facile, Regio- and Diastereoselective Synthesis of Spiro-Pyrrolidine and Pyrrolizine Derivatives and Evaluation of Their Antiproliferative Activities
    Almansour, Abdulrahman I.
    Kumar, Raju Suresh
    Beevi, Farzana
    Shirazi, Amir Nasrolahi
    Osman, Hasnah
    Ismail, Rusli
    Choon, Tan Soo
    Sullivan, Brian
    McCaffrey, Kellen
    Nahhas, Alaa
    Parang, Keykavous
    Ali, Mohamed Ashraf
    [J]. MOLECULES, 2014, 19 (07): : 10033 - 10055
  • [4] 1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2H-Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles
    Angyal, Aniko
    Demjen, Andras
    Harmat, Veronika
    Wolfling, Janos
    Puskas, Laszlo G.
    Kanizsai, Ivan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07) : 4273 - 4281
  • [5] Arumugam N., 2023, J. King Saud Univ. Sci
  • [6] Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds
    Askri, Sonia
    Dbeibia, Amal
    Mchiri, Chadlia
    Boudriga, Sarra
    Knorr, Michael
    Roulland, Emmanuel
    Laprevote, Olivier
    Saffon-Merceron, Nathalie
    Gharbi, Rafik
    [J]. APPLIED SCIENCES-BASEL, 2022, 12 (01):
  • [7] Synthesis, biological evaluation, density functional calculation and molecular docking analysis of novel spiropyrrolizidines derivatives as potential anti-microbial and anti-coagulant agents
    Askri, Sonia
    Edziri, Hayet
    Ben Hamouda, Manel
    Mchiri, Chadlia
    Gharbi, Rafik
    Abd El-Gawad, Hala H.
    El-Tahawy, Mohsen M. T.
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2022, 1250
  • [8] A three-component, general and practical route for diastereoselective synthesis of aza-spirocyclic pyrazolones via a decarboxylative annulation process
    Awasthi, Annapurna
    Yadav, Pushpendra
    Tiwari, Dharmendra Kumar
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (05) : 2374 - 2383
  • [9] Design, Synthesis and In Vitro Evaluation of Spirooxindole-Based Phenylsulfonyl Moiety as a Candidate Anti-SAR-CoV-2 and MERS-CoV-2 with the Implementation of Combination Studies
    Barakat, Assem
    Mostafa, Ahmed
    Ali, M.
    Al-Majid, Abdullah Mohammed
    Domingo, Luis R.
    Kutkat, Omnia
    Moatasim, Yassmin
    Zia, Komal
    Ul-Haq, Zaheer
    Elshaier, Yaseen A. M. M.
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (19)
  • [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
12345678910