Simple and Efficient Preparation of 2,5-Disubstituted Oxazoles via a Metal-Free-Catalyzed Cascade Cyclization

被引：147
|
作者：
Wan, Changfeng
Gao, Linfeng
Wang, Qiang
Zhang, Jintang
Wang, Zhiyong [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 17期
关键词：
SP(3) C-H; DIRECT ARYLATION; COPPER; INHIBITORS; OXIDATION;
D O I：
10.1021/ol101596s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.
引用
收藏
页码：3902 / 3905
页数：4
相关论文
共 50 条
  • [31] Synthesis of 2,5-disubstituted thiophenes via metal-free sulfur heterocyclization of 1,3-diynes with sodium hydrosulfide
    Tang, Jialiang
    Zhao, Xiaoming
    RSC ADVANCES, 2012, 2 (13) : 5488 - 5490
  • [32] Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions
    Li, Jun-Li
    Li, Hao-Yuan
    Zhang, Shan-Shan
    Shen, Shigang
    Yang, Xiu-Long
    Niu, Xiaoying
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21): : 14874 - 14886
  • [33] Palladium catalyzed α-arylation of methyl isobutyrate and isobutyronitrile:: an efficient synthesis of 2,5-disubstituted benzyl alcohol and amine intermediates
    Shetty, Rupa
    Moffett, Kristofer K.
    TETRAHEDRON LETTERS, 2006, 47 (46) : 8021 - 8024
  • [34] A mild and efficient synthesis of 2,5-disubstituted 2,3-dihydro-4-pyridones catalyzed by Yb(OTf)3
    Cheng, K
    Zeng, BQ
    Yu, ZP
    Gao, B
    Feng, XM
    SYNLETT, 2005, (06) : 1018 - 1020
  • [35] Synthesis of 2,4-Disubstituted Oxazoles and Thiazoles via Brønsted Acid-Catalyzed Cyclization of α-diazoketones with Amides
    Luo, Mengxiang
    Li, Lewan
    Chen, Shixin
    Yan, Qiongjiao
    Lv, Jian
    Zeng, Jie
    Wang, Haifeng
    Gu, Shuangxi
    Chen, Fener
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 5038 - 5048
  • [36] The regioselective synthesis of 2,5-and 4,5-disubstituted thiazoles via the cyclization of 2-oxo-2-(amino)ethanedithioates with isocyanides
    Ravi Singh, Krishna
    Santhosh, Chikkappaiahnayaka
    Swaroop, Toreshettahally R.
    Sadashiva, Maralinganadoddi P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (29) : 5771 - 5778
  • [37] Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes
    Chen, Zhengwang
    Huang, Gao
    Jiang, Huanfeng
    Huang, Huawen
    Pan, Xiaoyan
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04): : 1134 - 1139
  • [38] Regioselective Synthesis of 2,4-and 2,5-Disubstituted 1,3-Thiazoles from 2-Oxo-2-(amino)ethanedithioates via Base-Catalyzed Cyclization
    Singh, Krishna Ravi
    Santhosh, Chikkappaiahnayaka
    Sheela, Kalleshappa
    Sadashiva, Maralinganadoddi P.
    SYNTHESIS-STUTTGART, 2024, 56 (05): : 878 - 886
  • [39] Synthesis of 2,5-Disubstituted Pyrrolidine Alkaloids via A One-Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts
    Costa, Bruna Z.
    Galman, James L.
    Slabu, Iustina
    France, Scott P.
    Marsaioli, Anita J.
    Turner, Nicholas J.
    CHEMCATCHEM, 2018, 10 (20) : 4733 - 4738
  • [40] Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N-H free tetrazoles with boronic acids
    Li, Yu
    Gao, Lian-Xun
    Han, Fu-She
    CHEMICAL COMMUNICATIONS, 2012, 48 (21) : 2719 - 2721
12345