[3+2]-Cycloaddition of 2H-Azirines with Nitrosoarenes: Visible-Light-Promoted Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles

被引:67
|
作者
Cai, Bao-Gui [1 ]
Chen, Ze-Le [1 ]
Xu, Guo-Yong [3 ]
Xuan, Jun [1 ,3 ]
Xiao, Wen-Jing [2 ]
机构
[1] Anhui Univ, Coll Chem & Chem Engn, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Hefei 230601, Anhui, Peoples R China
[2] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[3] Anhui Univ, Inst Phys Sci & Informat Technol, Hefei 230601, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
SOLID-PHASE SYNTHESIS; PHOTOREDOX CATALYSIS; CYCLOADDITION; CYCLIZATION; CHEMISTRY; FUNCTIONALIZATION; DERIVATIVES; ANNULATION; 1,2,4-OXADIAZOLES; CYCLOPROPANES;
D O I
10.1021/acs.orglett.9b01416
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal [3 + 2]-cycloaddition reaction of 2H-azirines with nitrosoarenes has been achieved under irradiation by visible light with the assistance of organic dye photoredox catalyst. This method utilizes nitrosoarenes as efficient radical acceptors and provides a green and powerful method for a series of biologically important 1,2,4-oxadiazole derivatives in moderate to good yields.
引用
收藏
页码:4234 / 4238
页数:5
相关论文
共 50 条
  • [1] Synthesis of 2,5-dihydro-1,2,4-oxadiazoles through formal [3+2] cycloaddition of oxazoles with nitrosobenzene derivatives
    Suga, H
    Shi, XL
    Ibata, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (05) : 1231 - 1236
  • [2] [3+2] Cycloaddition of Oxaziridines with Nitriles: Synthesis of 2,3-Dihydro-1,2,4-Oxadiazoles
    Troisi, Luigino
    Ronzini, Ludovico
    Rosato, Francesca
    Videtta, Valeria
    [J]. SYNLETT, 2009, (11) : 1806 - 1808
  • [3] Visible-Light-Promoted [3+2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones
    Wang, Lijia
    Liu, Chuang
    Li, Lei
    Wang, Xin
    Sun, Ran
    Zhou, Ming-Dong
    Wang, He
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (06) : 719 - 724
  • [4] Mass spectrometric analysis of 1,2,4-oxadiazoles and 4,5-dihydro-1,2,4-oxadiazoles
    Srivastava, RM
    [J]. MASS SPECTROMETRY REVIEWS, 2005, 24 (03) : 328 - 346
  • [5] Gold-Catalyzed Formal [3+2] Cycloaddition of Ynamides with 4,5-Dihydro-1,2,4-oxadiazoles: Synthesis of Functionalized 4-Aminoimidazoles
    Xu, Wei
    Wang, Gaonan
    Sun, Ning
    Liu, Yuanhong
    [J]. ORGANIC LETTERS, 2017, 19 (12) : 3307 - 3310
  • [6] ZnCl2-Catalyzed [3+2] Cycloaddition of Benzimidates and 2H-Azirines for the Synthesis of Imidazoles
    Shi, Shoujie
    Xu, Kang
    Jiang, Cheng
    Ding, Zhenhua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14791 - 14796
  • [7] [3+2]-Cycloaddition Reaction between Chiral Oxaziridines and Nitriles: Enantioselective Synthesis of 2,3-Dihydro-1,2,4-oxadiazoles
    Troisi, Luigino
    Caccamese, Salvatore
    Pilati, Tullio
    Videtta, Valeria
    Rosato, Francesca
    [J]. SYNTHESIS-STUTTGART, 2010, (18): : 3211 - 3216
  • [8] SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles
    Dong Zou
    Lishe Gan
    Fan Yang
    Huan Wang
    Youge Pu
    Jie Li
    Patrick J. Walsh
    [J]. Nature Communications, 12
  • [9] TiO2-Nanoparticles Catalyzed Synthesis of New Trifluoromethyl-4,5-dihydro-1,2,4-oxadiazoles and Trifluoromethyl-1,2,4-oxadiazoles
    Darehkordi, Ali
    Ramezani, Mahin
    Rahmani, Fariba
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (07) : 1702 - 1708
  • [10] SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles
    Zou, Dong
    Gan, Lishe
    Yang, Fan
    Wang, Huan
    Pu, Youge
    Li, Jie
    Walsh, Patrick J.
    [J]. NATURE COMMUNICATIONS, 2021, 12 (01)