Metal free C-O bond cleavage: a new strategy for the synthesis of substituted oxazoles

被引:1
|
作者
Li, Shengwang [1 ]
Liu, Guiqin [1 ]
Zhang, Zheyan [1 ]
Chen, Ruiling [2 ]
Tian, Haiying [2 ]
Wang, Huifeng [1 ]
Chen, Xiuling [1 ]
机构
[1] Hubei Univ Sci & Technol, Hubei Key Lab Radiat Chem & Funct Mat, Xianning 437100, Peoples R China
[2] Changzhi Med Coll, Sch Pharm, Changzhi 046000, Peoples R China
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; ETHERS; OXYGENATION; CYCLIZATION; ACTIVATION; KETONES; AZOLES; ESTERS; CARBON;
D O I
10.1039/d4ra05122j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A strategy for the efficient metal-free C-O bond cleavage of ester using amines for the synthesis of substituted oxazoles was developed for the first time. The synthesis proceeded smoothly under metal-free conditions, combining C-O bond cleavage as well as C-N and C-O bond formation in one pot to yield desired products in moderate to excellent yields, and accommodated a wide range of functional groups and substrates. A strategy for C-O bond cleavage of ester for the synthesis of substituted oxazoles was developed. The synthesis proceeded smoothly under metal-free conditions, combining C-O bond cleavage, C-N and C-O bond formation in one pot.
引用
收藏
页码:28210 / 28214
页数:5
相关论文
共 50 条
  • [1] Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity
    Cornella, Josep
    Zarate, Cayetana
    Martin, Ruben
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (23) : 8081 - 8097
  • [2] Transition-metal-free aerobic C-O bond formation via C-N bond cleavage
    Guo, Lirong
    Liu, Fengting
    Wang, Liying
    Yuan, Hairui
    Feng, Lei
    Lu, Haifeng
    Gao, Hongyin
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09): : 1077 - 1081
  • [3] CLEAVAGE OF C-O BOND BY ORGANOMAGNESIUM COMPOUNDS
    TROFIMOV, BA
    KOROSTOVA, SE
    USPEKHI KHIMII, 1975, 44 (01) : 75 - 103
  • [4] Metal-free C-N bond-forming reaction: straightforward synthesis of anilines, through cleavage of aryl C-O bond and amide C-N bond
    Yu, Jianzhong
    Zhang, Peizhi
    Wu, Jun
    Shang, Zhicai
    TETRAHEDRON LETTERS, 2013, 54 (24) : 3167 - 3170
  • [5] Photolytic C-O Bond Cleavage with Quantum Dots
    Enright, Michael J.
    Gilbert-Bass, Kito
    Sarsito, Harrison
    Cossairt, Brandi M.
    CHEMISTRY OF MATERIALS, 2019, 31 (07) : 2677 - 2682
  • [6] Regioselective C-O bond cleavage reactions of acetals
    Luh, TY
    PURE AND APPLIED CHEMISTRY, 1996, 68 (03) : 635 - 638
  • [8] Synergistic effects of Ni and acid sites for hydrogenation and C-O bond cleavage of substituted phenols
    Song, Wenji
    Liu, Yuanshuai
    Barath, Eszter
    Zhao, Chen
    Lercher, Johannes A.
    GREEN CHEMISTRY, 2015, 17 (02) : 1204 - 1218
  • [9] Direct transition-metal-free intramolecular C-O bond formation: synthesis of benzoxazole derivatives
    Peng, Jinsong
    Zong, Cuijuan
    Ye, Min
    Chen, Tonghui
    Gao, Dewei
    Wang, Yufeng
    Chen, Chunxia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1225 - 1230
  • [10] Base metal-catalyzed, additive-free C-O bond cleavage of β-O-4 lignin model compounds
    Brown, Orain
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257