[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
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 11期
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
  • [21] 2H-Azirines: Recent Progress in Synthesis and Applications
    Xu, Fen
    Zeng, Fan-Wang
    Luo, Wen-Jie
    Zhang, Shi-Yu
    Huo, Jia-Qi
    Li, Ya-Peng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (11)
  • [22] Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles
    Zhao, Mi-Na
    Ren, Zhi-Hui
    Yang, De-Suo
    Guan, Zheng-Hui
    ORGANIC LETTERS, 2018, 20 (05) : 1287 - 1290
  • [23] Visible-Light-Promoted Fluoroalkylative Cyclization of N-Allyl-4,5-dihydro-3H-1-benzazepin-2-amines: Effective Synthesis of Fluoroalkylated Imidazobenzazepines
    Danyliuk, Ivanna Yu.
    Tolmachova, Valentyna S.
    Shishkina, Svitlana V.
    Vovk, Mykhailo V.
    CHEMISTRYSELECT, 2023, 8 (13):
  • [24] Photocatalyzed facile synthesis of 2,5-diaryl 1,3,4-oxadiazoles with polyaniline-g-C3N4-TiO2 composite under visible light
    Wang, Liang
    Wang, Yaoyao
    Chen, Qun
    He, Mingyang
    TETRAHEDRON LETTERS, 2018, 59 (15) : 1489 - 1492
  • [25] Study on the interaction of triaryl-dihydro-1,2,4-oxadiazoles with α-glucosidase
    Khosravi, Arefeh
    Vaezi, Gholamhassan
    Hojati, Vida
    Abdi, Khosrou
    DARU-JOURNAL OF PHARMACEUTICAL SCIENCES, 2020, 28 (01) : 109 - 117
  • [26] Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3+2] cycloaddition of 2H-azirines and ynamides
    Shcherbakov, Nikolay, V
    Titov, Gleb D.
    Chikunova, Elena, I
    Filippov, Ilya P.
    Rostovskii, Nikolai, V
    Kukushkin, Vadim Yu
    Dubovtsev, Alexey Yu
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5133 - 5140
  • [27] Energetic 1,2,4-oxadiazoles: synthesis and properties
    Shaferov, Alexander V.
    Fershtat, Leonid L.
    RUSSIAN CHEMICAL REVIEWS, 2024, 93 (02)
  • [28] Synthesis of 3-dinitromethyl-1,2,4-oxadiazoles from dinitroacetamidoximes
    Frumkin, A. E.
    Suponitsky, K. Yu
    Sheremetev, A. B.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (09) : 2012 - 2015
  • [29] [3+2] Redox-Neutral Cycloaddition of Nitrocyclopropanes with Styrenes by Visible-Light Photocatalysis
    Wang, Chengfeng
    Ren, Xiang
    Xie, Hujun
    Lu, Zhan
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (27) : 9676 - 9680
  • [30] Copper-catalyzed 2,3-dihydro-1,2,4-triazoles synthesis through [3+2]-cycloaddition of nitrile ylides with azodicarboxylates
    Cai, Bao-Gui
    Li, Qian
    Xuan, Jun
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (03): : 191 - 194
12345