1,3-Dipolar Cycloaddition of Nitrones with 5-Methylenehydantoins: Synthesis and Transformation of New Spirohydantoin Derivatives

被引：11
|
作者：
Bahy, Amira [1 ]
Kacem, Yakdhane [1 ]
Ben Hassine, Bechir [1 ]
机构：
[1] Fac Sci, Lab Asymmetr Organ Synth & Homogeneous Catalysis, Monastir 5019, Tunisia
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 09期
关键词：
1; 3-Dipolar cycloaddition; 5-methylenehydantoins; nitrones; regioselectivity; stereoselectivity; METHYLENE-GAMMA-BUTYROLACTONES; ENANTIOSELECTIVE SYNTHESIS; SOLUTION-PHASE; ALPHA; HYDANTOCIDIN; ANALOGS; STEREOSELECTIVITY; (+)-HYDANTOCIDIN; GLUCOFURANOSE; METABOLITE;
D O I：
10.1080/00397910903097237
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of various acyclic nitrones with 5-methylenehydantoin derivatives afforded new chiral spiroadducts in good yields. All the spirohydantoins were obtained through a regio- and stereospecific pathway, and the spirocarbon atom was linked to the isoxazolidine oxygen atom. A representative example of the reduction of the spirohydantoin 8 with Zn/AcOH led to the substituted 1,3-aminoalcohol hydantoin 20.
引用
收藏
页码：1377 / 1390
页数：14
相关论文
共 50 条
  • [41] Copper(I)-Catalyzed Asymmetric 1,3-Dipolar [3+4]Cycloaddition of Nitrones with Azoalkenes
    Wei, Liang
    Yao, Lu
    Wang, Zuo-Fei
    Li, Hua
    Tao, Hai-Yan
    Wang, Chun-Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3748 - 3752
  • [42] The asymmetric organocatalytic 1,3-dipolar cycloaddition of alkyl pyruvate-derived nitrones and α,β-unsaturated aldehydes
    Weselinski, Lukasz
    Kalinowska, Eleonora
    Jurczak, Janusz
    TETRAHEDRON-ASYMMETRY, 2012, 23 (3-4) : 264 - 270
  • [43] Intramolecular 1,3-dipolar cycloaddition of N-alkenyl nitrones en route to glycosyl piperidines
    Marca, Eduardo
    Delso, Ignacio
    Tejero, Tomas
    Vazquez, Jesus T.
    Dorta, Rosa L.
    Merino, Pedro
    TETRAHEDRON LETTERS, 2009, 50 (51) : 7152 - 7155
  • [44] Synthesis and characterization of 5-substituted novel isoxazolidines derived from 1,3-dipolar cycloaddition of nitrones with olefins: Studies of antibacterial and antifungal activities
    Kumar, KRR
    Mallesha, H
    Rangappa, KS
    SYNTHETIC COMMUNICATIONS, 2003, 33 (09) : 1545 - 1555
  • [45] Synthesis of spiroisoxazolidinyl-benzoisothiazolines by 1,3-dipolar cycloaddition of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrones
    Cao, Guorui
    Zhou, Shizheng
    Teng, Dawei
    TETRAHEDRON, 2017, 73 (16) : 2329 - 2333
  • [46] Intramolecular low-temperature 1,3-dipolar cycloadditions of nitrones: synthesis of chromano-heterocycles
    Singh, Gurpinder
    Ishar, M. P. S.
    Gupta, Vivek
    Singh, Gurmit
    Kalyan, Mohit
    Bhella, Surinderjit Singh
    TETRAHEDRON, 2007, 63 (22) : 4773 - 4778
  • [47] 1,3-dipolar cycloaddition reaction of 3,4-dihydro-β-carboline 2-oxide
    Moriyama, S
    Vallée, Y
    SYNTHESIS-STUTTGART, 1998, (04): : 393 - 404
  • [48] Cyclopropenes and methylenecyclopropanes in 1,3-dipolar cycloaddition reactions
    Molchanov, A. P.
    Efremova, M. M.
    Kuznetsov, M. A.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (04) : 620 - 650
  • [49] Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
    Wang, Bo-Ran
    Li, Yan-Bo
    Zhang, Qi
    Gao, Dingding
    Tian, Ping
    Li, Qinghua
    Yin, Liang
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [50] Aldimines of 5-aminouracil as reagents in 1,3-dipolar cycloaddition reaction
    Jakubiec, Dominika
    Walczak, Krzysztof Z.
    MONATSHEFTE FUR CHEMIE, 2011, 142 (11): : 1155 - 1161
12345