Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides

被引：6
|
作者：
Chen, Yuan [1 ]
Fuyue, Liuting [1 ]
Wang, Gangqiang [1 ]
Wang, Hang [1 ]
Lu, Chun [1 ]
Guo, Haibing [1 ]
St Amant, Chiara [2 ]
Sun, Shaofa [1 ]
Xing, Yalan [2 ]
机构：
[1] Hubei Univ Sci & Technol, Sch Nucl Technol & Chem & Biol, Nonpower Nucl Technol Collaborat Innovat Ctr, Xianning 437100, Peoples R China
[2] William Paterson Univ New Jersey, Dept Chem, 300 Pompton Rd, Wayne, NJ 07470 USA
来源：
NEW JOURNAL OF CHEMISTRY | 2019年 / 43卷 / 11期
关键词：
AZA-OXYALLYLIC CATIONS;
D O I：
10.1039/c9nj00030e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.
引用
收藏
页码：4329 / 4332
页数：4
相关论文
共 50 条
  • [1] ONE-STEP SYNTHESIS OF 3,5-DIIMINO-1,2,4-OXADIAZOLIDINES
    SCHECKER, HG
    ZINNER, G
    [J]. ARCHIV DER PHARMAZIE, 1981, 314 (03) : 268 - 271
  • [2] SYNTHESIS OF N-2-ALKYL(ARYL)-3,5-DIOXO-1,2,4-OXADIAZOLIDINES
    KRAUS, JL
    DUGENET, P
    YAOUANC, JJ
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) : 971 - 973
  • [3] SYNTHESIS AND REACTIONS OF N2-UNSUBSTITUTED 3,5-DIOXO-1,2,4-OXADIAZOLIDINES .40.
    ZINNER, G
    HITZE, M
    [J]. ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1970, 303 (02): : 139 - &
  • [4] Annulation of phosphole sulfides via [3+2] cycloaddition with nitrones
    Hou, Yueshan
    Cui, Mingyue
    Zhang, Keke
    Chen, Lihui
    Tian, Rongqiang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022,
  • [5] Annulation of phosphole sulfides via [3+2] cycloaddition with nitrones
    Hou, Yueshan
    Cui, Mingyue
    Zhang, Keke
    Chen, Lihui
    Tian, Rongqiang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23): : 6606 - 6610
  • [6] Synthesis of 4-Phosphinylpyrrolidin-3-ones via [3+2] Cycloaddition of Nitrones with Phosphinylallenes
    Hammami, Rayhane
    Maldivi, Pascale
    Philouze, Christian
    Carret, Sebastien
    Darses, Benjamin
    Touil, Soufiane
    Poisson, Jean-Francois
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) : 1385 - 1390
  • [7] [3+2]-Dipolar Cycloaddition of Nitrones to Pyrroloquinoxalinetriones
    Stepanova, E. E.
    Dmitriev, M., V
    Maslivets, A. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (01) : 32 - 37
  • [8] [3+2]CYCLOADDITION REACTIONS OF NITRONES WITH ISOTHIOCYANATES
    ZINNER, G
    EGHTESSAD, E
    [J]. ARCHIV DER PHARMAZIE, 1979, 312 (11) : 907 - 913
  • [9] [3+2]-Dipolar Cycloaddition of Nitrones to Pyrroloquinoxalinetriones
    E. E. Stepanova
    M. V. Dmitriev
    A. N. Maslivets
    [J]. Russian Journal of Organic Chemistry, 2021, 57 : 32 - 37
  • [10] Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived phosphonates via [3+2] cycloaddition
    Chalyk, Bohdan A.
    Sosedko, Alona S.
    Volochnyuk, Dmitriy M.
    Tolmachev, Andrey A.
    Gavrilenko, Konstantin S.
    Liashuk, Oleksandr S.
    Grygorenko, Oleksandr O.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (47) : 9152 - 9164
12345