Copper-catalyzed synthesis of phenolic compounds with DMSO as the methylene source

被引：3
|
作者：
Luo, Run [1 ]
Guo, Lina [1 ]
Liu, Wenjie [1 ,2 ]
Wang, Shaohua [1 ,2 ]
机构：
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Peoples R China
[2] Guangdong Cosmet Engn & Technol Res Ctr, Guangzhou, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 11期
关键词：
CuSO4· 5H(2)O; cyclization; 1; 3-dicarbonyl; DMSO; phenolic compounds;
D O I：
10.1080/00397911.2021.1902536
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The application of DMSO as an ideal source of carbon is highly attractive. A simple and novel protocol has been developed for the synthesis of phenolic compounds via CuSO4 center dot 5H(2)O-catalyzed cyclization of 1,3-dicarbonyl compounds with DMSO. It was found that the unsymmetrical 1,3-dicarbonyl compounds always gave a mixture of two isomeric products. In addition, the deuterium-labeling experiments revealed that the C2 in benzene rings resulted from DMSO.
引用
收藏
页码：1712 / 1722
页数：11
相关论文
共 50 条
  • [1] Copper-catalyzed cyanation of aryl iodide with the combined cyanide source of urea and DMSO
    Zheng, Kui
    Liu, Bin
    Chen, Shuyou
    Chen, Fan
    TETRAHEDRON LETTERS, 2013, 54 (38) : 5250 - 5252
  • [2] The copper-catalyzed selective monoalkylation of active methylene compounds with alkylsilyl peroxides
    Lv, Jiamin
    Xu, Weiping
    Lu, Hanbin
    Kato, Terumasa
    Liu, Yan
    Maruoka, Keiji
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (12) : 2658 - 2662
  • [3] COPPER-CATALYZED REACTION OF ARYL IODIDES WITH ACTIVE METHYLENE-COMPOUNDS
    OKURO, K
    FURUUNE, M
    MIURA, M
    NOMURA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26): : 7606 - 7607
  • [4] Copper-Catalyzed Domino Reactions for the Synthesis of Cyclic Compounds
    Liao, Qian
    Yang, Xianghua
    Xi, Chanjuan
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18): : 8507 - 8515
  • [5] Copper-Catalyzed Synthesis of N-Heterocyclic Compounds
    Liu, Tao
    Fu, Hua
    SYNTHESIS-STUTTGART, 2012, 44 (18): : 2805 - 2824
  • [6] Synthesis of Functionalized γ-Lactams via Copper-Catalyzed Intramolecular C-Vinylation of Activated Methylene Compounds
    Chen Liqun
    Shi Min
    Li Chaozhong
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (09) : 1660 - 1664
  • [7] Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source
    Jia, Jing
    Jiang, Qing
    Zhao, An
    Xu, Bin
    Liu, Qiang
    Luo, Wei-Ping
    Guo, Can-Cheng
    SYNTHESIS-STUTTGART, 2016, 48 (03): : 421 - 428
  • [8] Copper-catalyzed synthesis of 4-methylene-4,5-dihydrooxazoles
    Ferraro, Mark
    Fennie, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [9] Copper-catalyzed coupling of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones
    Pal, Arpan
    Hussaini, Syed
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [10] Copper-catalyzed decarboxylative methylthiolation of aromatic carboxylate salts with DMSO
    Hu, Liang
    Wang, Dadian
    Chen, Xiang
    Yu, Lin
    Yu, Yongqi
    Tan, Ze
    Zhu, Gangguo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (27) : 5674 - 5679
12345