Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C-H Activation/O-Annulation

被引：19
|
作者：
Nale, Sagar D. [1 ]
Maiti, Debabrata [2 ]
Lee, Yong Rok [1 ]
机构：
[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 38541, South Korea
[2] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 07期
基金：
新加坡国家研究基金会;
关键词：
NATURAL-PRODUCTS; ROOT BARK; SALICYLALDEHYDES; BIOSYNTHESIS; CONSTITUENTS; DERIVATIVES; ALDEHYDES; CHROMONES; ALKYNES; FRUITS;
D O I：
10.1021/acs.orglett.1c00391
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile and efficient strategy for obtaining functionalized and multihydroxylated xanthones via Rh catalysis under redox-neutral conditions is developed. Diverse salicylaldehydes bearing heterocycles, aromatics, and fused aromatics can be rapidly coupled with 1,4-benzoquinones or 1,4-hydroquinones to afford valuable xanthones via cascade C-H/O-H functionalization and annulation. This protocol provides a rapid synthetic approach to obtain biologically active materials through late-stage functionalization and prepares natural products such as subelliptenone, pruniflorone N, and ravenelin.
引用
收藏
页码：2465 / 2470
页数：6
相关论文
共 50 条
  • [1] Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction
    Lv, Ningning
    Chen, Zhengkai
    Liu, Yue
    Liu, Zhanxiang
    Zhang, Yuhong
    ORGANIC LETTERS, 2017, 19 (10) : 2588 - 2591
  • [2] Rh(III)-Catalyzed C-H Activation/O-Annulation for Construction of Divergent Spirosuccinimide and Maleimide-Fused Isochromenes
    Kamaraj, Eswaran
    Roy, Prasanta
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3915 - 3926
  • [3] Rh-Catalyzed aldehydic C-H alkynylation and annulation
    Rao, Maddali L. N.
    Ramakrishna, Boddu S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (07) : 1402 - 1411
  • [4] Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade
    Gao, Qian-Ci
    Li, Yi-Fei
    Xuan, Jun
    Hu, Xiao-Qiang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 100 - 106
  • [5] Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones
    Fang, Taibei
    Zhang, Shiwen
    Ye, Qingqing
    Kong, Shuwen
    Yang, Tingting
    Tang, Kaijie
    He, Xinwei
    Shang, Yongjia
    MOLECULES, 2022, 27 (23):
  • [6] Recent advances in the Rh-catalyzed cascade arene C-H bond activation/annulation toward diverse heterocyclic compounds
    Wang, Chang
    Chen, Fan
    Qian, Pengcheng
    Cheng, Jiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (08) : 1705 - 1721
  • [7] Tandem Rh-Catalyzed [4+2] Vinylic C-H O-Annulation of Exocyclic Enones with Alkynes and 1,5-H Shift
    Zhao, Yinsong
    Yu, Chuangui
    Wang, Tianbao
    She, Zhijie
    Zheng, Xuesong
    You, Jingsong
    Gao, Ge
    ORGANIC LETTERS, 2018, 20 (04) : 1074 - 1077
  • [8] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
    Hou, Xinjiao
    Wang, Run
    Fang, Feifei
    Qu, Zhiyan
    Zhou, Jianhui
    Yu, Ting
    Wang, Dechuan
    Liu, Hong
    Zhou, Yu
    ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
  • [9] Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C-H Annulation with Alkynes
    Wang, Qiang
    Zhang, Wen-Wen
    Zheng, Chao
    Gu, Qing
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (01) : 114 - 120
  • [10] Rh-catalyzed chemo-, stereo- and regioselective C-H cascade annulation of indolyloxopropanenitriles for pyranoindoles
    Kotipalli, Ramesh
    Babu, Undamatla Suri
    Nanubolu, Jagadeesh Babu
    Reddy, Maddi Sridhar
    CHEMICAL COMMUNICATIONS, 2023, 59 (67) : 10137 - 10140
12345