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

被引:68
|
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] 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
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (06) : 719 - 724
  • [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
    SYNLETT, 2009, (11) : 1806 - 1808
  • [3] Visible-Light-Promoted Click [3+2] Cycloaddition of Aziridine with Alkyne: An Efficient Synthesis of Dihydropyrrolidine
    Kapoor, Ritu
    Chawla, Ruchi
    Verma, Ankit
    Keshari, Twinkle
    Siddiqui, I. R.
    SYNLETT, 2023, 34 (13) : 1621 - 1625
  • [4] 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.
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [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
    ORGANIC LETTERS, 2017, 19 (12) : 3307 - 3310
  • [6] Organophotoredox-mediated Formal [3+2]-Cycloaddition of 2H-Azirines with Aryldiazonium Salts: Direct Access to Trisubstituted 1,2,4-Triazoles
    Mishra, Poornima
    Kumar, Prashant
    Srivastava, Oj Shikhar
    Rastogi, Namrata
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (07)
  • [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
    SYNTHESIS-STUTTGART, 2010, (18): : 3211 - 3216
  • [8] Visible light-driven [3+3] annulation reaction of 2H-azirines with Huisgen zwitterions and synthesis of 1,2,4-triazines
    Cao, Shixuan
    Tang, Tong
    Li, Jiatian
    He, Zhengjie
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (12) : 3342 - 3347
  • [9] Ruthenium-Catalyzed [3+2] Cycloaddition of 2H-Azirines with Alkynes: Access to Polysubstituted Pyrroles
    Li, Tengfei
    Yan, Hao
    Li, Xincheng
    Wang, Chunxiang
    Wan, Boshun
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 12031 - 12037
  • [10] Visible light-promoted synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones via [3+2] cycloaddition reaction of 2H-azirines with maleimides
    Guo, Hao
    Wang, Huahao
    Zhao, Hongyi
    Zhang, Dongfeng
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (12) : 5634 - 5638