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
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
  • [31] Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions
    Hashimoto, Takuya
    Maruoka, Keiji
    [J]. CHEMICAL REVIEWS, 2015, 115 (11) : 5366 - 5412
  • [32] A Facile Synthesis of Functionalized Dispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction
    He, Jun
    Ouyang, Guang
    Yuan, Zhixiang
    Tong, Rongsheng
    Shi, Jianyou
    Ouyang, Liang
    [J]. MOLECULES, 2013, 18 (05) : 5142 - 5154
  • [33] 1,3-Dipolar cycloaddition approach to novel dispiro[pyrazolidine-4,3′-pyrrolizidine-2′,3"-indoline]-2",3,5-triones
    Hussein, Essam M.
    Ahmed, Saleh A.
    El Guesmi, Nizar
    Khairou, Khalid S.
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2017, (06) : 346 - 351
  • [34] Synthesis of Spiro-oxindole Analogs Engrafted Pyrazole Scaffold as Potential Alzheimer's Disease Therapeutics: Anti-oxidant, Enzyme Inhibitory and Molecular Docking Approaches
    Islam, Mohammad Shahidul
    Al-Majid, Abdullah Mohammed
    Sholkamy, Essam Nageh
    Yousuf, Sammer
    Ayaz, Muhammad
    Nawaz, Asif
    Wadood, Abdul
    Rehman, Ashfaq Ur
    Verma, Ved Prakash
    Rahman, A. F. M. Motiur
    Barakat, Assem
    [J]. CHEMISTRYSELECT, 2022, 7 (36):
  • [35] Ultrasound-Assisted Sequential Multicomponent Strategy for the Combinatorial Synthesis of Novel Coumarin Hybrids
    Kanchithalaivan, Selvaraj
    Sumesh, Remani Vasudevan
    Kumar, Raju Ranjith
    [J]. ACS COMBINATORIAL SCIENCE, 2014, 16 (10) : 566 - 572
  • [36] Karlsson S, 2001, ORG PREP PROCED INT, V33, P105
  • [37] Novel benzosuberone conjugates as potential anti-proliferative agents: Design, synthesis and molecular docking studies
    Kasaboina, Suresh
    Bollu, Rajitha
    Ramineni, Venkatesh
    Gomedhika, P. Mary
    Korra, Kavitha
    Basaboina, Sai Roopika
    Holagunda, Uma Devi
    Nagarapu, Lingaiah
    Dumala, Naresh
    Grover, Paramjit
    Bathini, Raju
    Vijjulatha, M.
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2019, 1180 : 355 - 362
  • [38] Microwave accelerated azomethine ylide cycloaddition with Baylis-Hillman adducts
    Keesari, Nagarjuna Reddy
    Mudavath, Somanath
    Rao, M. V. Krishna
    Sridhar, Balasubramanian
    Subba Reddy, B. V.
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (07) : 973 - 979
  • [39] Asymmetric 1,3-dipolar cycloadditions of acrylamides
    Kissane, Marie
    Maguire, Anita R.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 845 - 883
  • [40] 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles
    Korotaev, Vladislav Yu
    Zimnitskiy, Nikolay S.
    Denikaev, Andrey D.
    Barkov, Alexey Yu
    Kutyashev, Igor B.
    Sosnovskikh, Vyacheslav Ya
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (01) : 81 - 91