Iron-Catalyzed Cycloaddition of Amides and 2,3-Diaryl-2H-azirines To Access Oxazoles via C-N Bond Cleavage

被引:9
|
作者
Zhao, Mi-Na [1 ]
Ning, Gui-Wan [1 ]
Yang, De-Suo [1 ]
Fan, Ming-Jin [1 ]
Zhang, Sheng [1 ]
Gao, Peng [1 ]
Zhao, Li-Fang [1 ]
机构
[1] Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shaanxi Key Lab Phytochem, Baoji 721013, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 03期
基金
中国博士后科学基金;
关键词
D O I
10.1021/acs.joc.0c02843
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient iron-catalyzed cycloaddition reaction using readily available 2,3-diaryl-2H-azirines and primary amides is reported. A wide range of trisubstituted oxazoles could be achieved in good yields with good functional group compatibility. In this transformation, two C-N bonds were cleaed and new C-N and C-O bonds were formed.
引用
收藏
页码:2957 / 2964
页数:8
相关论文
共 50 条
  • [1] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [2] Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C-N bond cleavage
    Cui, Ming
    Wu, Hongxiang
    Jian, Junsheng
    Wang, Hui
    Liu, Chao
    Daniel, Stelck
    Zeng, Zhuo
    CHEMICAL COMMUNICATIONS, 2016, 52 (81) : 12076 - 12079
  • [3] Iron-Catalyzed C-N Bond Formation via the Beckmann Rearrangement
    Jefferies, Latisha R.
    Weber, Savannah R.
    Cook, Silas P.
    SYNLETT, 2015, 26 (03) : 331 - 334
  • [4] Palladium-Catalyzed C-N Bond Cleavage of 2H-Azirines for the Synthesis of Functionalized α-Amido Ketones
    Xu, Fen
    Si, Xiao-Ju
    Song, Yuan-Yuan
    Wang, Xing-Dong
    Liu, Chun-Sen
    Geng, Peng-Fei
    Du, Miao
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 2200 - 2208
  • [5] 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
  • [6] Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates
    Zhao, Mi-Na
    Guan, Zheng-Hui
    ORGANIC SYNTHESES, 2019, 96 : 66 - +
  • [7] Iron-Catalyzed Synthesis of 2-Vinylquinolines via sp3 C-H Functionalization and Subsequent C-N Cleavage
    Li, Yunfeng
    Guo, Fengfeng
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (03) : 534 - 537
  • [8] Iron-Catalyzed C?H and C?C Bond Cleavage: A Direct Approach to Amides from Simple Hydrocarbons
    Qin, Chong
    Zhou, Wang
    Chen, Feng
    Ou, Yang
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (52) : 12595 - 12599
  • [9] An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C-C Bond Cleavage
    Ou, Yang
    Qin, Chong
    Song, Song
    Jiao, Ning
    SYNTHESIS-STUTTGART, 2015, 47 (19): : 2971 - 2975
  • [10] Palladium(II)-Catalyzed C(sp2)-H Bond Activation/C-N Bond Cleavage Annulation of N-Methoxy Amides and Arynes
    Cheng, Xiu-Fen
    Yu, Ting
    Liu, Yi
    Wang, Nan
    Chen, Zhenzhen
    Zhang, Guang-Lu
    Tong, Lili
    Tang, Bo
    ORGANIC LETTERS, 2022, 24 (11) : 2087 - 2092