Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes

被引:17
|
作者
Li, Liang [1 ,2 ,3 ]
Wang, Guan-Wu [1 ,2 ]
机构
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Hefei Normal Univ, Dept Chem & Chem Engn, Hefei 230601, Anhui, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 20期
基金
中国国家自然科学基金;
关键词
CARBONYLATIVE CYCLIZATION REACTIONS; PALLADIUM-CATALYZED ANNULATION; H BOND FUNCTIONALIZATION; C-H; MEDICINAL MECHANOCHEMISTRY; EFFICIENT SYNTHESIS; PROMOTED SYNTHESIS; INTERNAL ALKYNES; SUZUKI-MIYAURA; CARBOANNULATION;
D O I
10.1021/acs.joc.1c01472
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPAR gamma agonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.
引用
收藏
页码:14102 / 14112
页数:11
相关论文
共 50 条
  • [1] Solvent-free mechanochemical synthesis of diacylfuroxans
    Gu, Zhen-Zhen
    Guo, Feng-Chao
    Zhang, Pu
    Qin, Yu-Jun
    Guo, Zhi-Xin
    TETRAHEDRON LETTERS, 2019, 60 (26) : 1687 - 1690
  • [2] Solvent-free biocatalytic amidation of carboxylic acids
    Prasad, AK
    Husain, M
    Singh, BK
    Gupta, RK
    Manchanda, VK
    Olsen, CE
    Parmar, VS
    TETRAHEDRON LETTERS, 2005, 46 (26) : 4511 - 4514
  • [3] Solvent-free mechanochemical synthesis of phosphonium salts
    Balema, VP
    Wiench, JW
    Pruski, M
    Pecharsky, VK
    CHEMICAL COMMUNICATIONS, 2002, (07) : 724 - 725
  • [4] Solvent-Free Mechanochemical Synthesis of Aryl Glycosides
    Patil, Premanand Ramrao
    Kartha, K. P. Ravindranathan
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2008, 27 (07) : 411 - 419
  • [5] Solvent-free mechanochemical synthesis of glycosylated curcumin
    Sarala, Garikapati
    Kartha, K. P. Ravindranathan
    TRENDS IN CARBOHYDRATE RESEARCH, 2016, 8 (03) : 19 - 28
  • [6] Solvent-free mechanochemical synthesis of dithiophosphonic acids and corresponding nickel(II) complexes
    Ajayi, Tomilola J.
    Pillay, Michael N.
    van Zyl, Werner E.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (11) : 1205 - 1211
  • [7] A solvent-free mechanochemical synthesis of polyaromatic hydrocarbon derivatives
    Wang, Cong
    Hill, Malik
    Theard, Brandon
    Mack, James
    RSC ADVANCES, 2019, 9 (48) : 27888 - 27891
  • [8] Solvent-free mechanochemical synthesis of organic proton conducting salts incorporating imidazole and dicarboxylic acids
    Zhou, Yating
    Koedtruad, Anucha
    Tan, Zhenhong
    Zhang, Dong
    Bao, Lingxiang
    Yue, Yajun
    Wu, Jianyuan
    Xu, Juping
    Xia, Yuanguang
    Yin, Wen
    Avdeev, Maxim
    Kan, Wang Hay
    Kamiyama, Takashi
    Miao, Ping
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2023, 42 (05)
  • [9] Mechanochemical solvent-free synthesis of metal-organic frameworks
    James, Stuart L.
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 : C40 - C40
  • [10] Mechanochemical reaction pathways in solvent-free synthesis of ZSM-5
    Nada, Majid H.
    Gillan, Edward G.
    Larsen, Sarah C.
    MICROPOROUS AND MESOPOROUS MATERIALS, 2019, 276 : 23 - 28