Rh(III)-Catalyzed C-H Activation/O-Annulation for Construction of Divergent Spirosuccinimide and Maleimide-Fused Isochromenes

被引：3
|
作者：
Kamaraj, Eswaran [1 ]
Roy, Prasanta [1 ]
Lee, Yong Rok [1 ]
机构：
[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 38541, South Korea
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 22期
基金：
新加坡国家研究基金会;
关键词：
Rhodium; Isochromene; Maleimide; Itaconimide; C-H activation; 5+1 Annulation; CATALYZED OXIDATIVE ANNULATION; NATURAL-PRODUCTS; FUNCTIONALIZATION; DERIVATIVES; ALKYLATION; INHIBITORS; ALKALOIDS; BONDS;
D O I：
10.1002/adsc.202300803
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A rhodium-catalyzed [5+1] cycloaddition via C-H activation/O-annulation strategy for synthesizing biologically interesting isochromenes is presented. This protocol selectively provides divergently functionalized isochromenes containing spirosuccinimide and maleimide scaffolds according to the maleimides and itaconimides used as the substrates. This methodology exhibits an extensive substrate scope, remarkable functional group tolerance, and high regioselectivity.
引用
收藏
页码：3915 / 3926
页数：12
相关论文
共 50 条
  • [1] Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C-H Activation/O-Annulation
    Nale, Sagar D.
    Maiti, Debabrata
    Lee, Yong Rok
    ORGANIC LETTERS, 2021, 23 (07) : 2465 - 2470
  • [2] 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
  • [3] Construction of Peptide-Isoquinolone Conjugates via Rh(III)- Catalyzed C-H Activation/Annulation
    Song, Liangliang
    Lv, Zhenwei
    Li, Yan
    Zhang, Kui
    Van der Eycken, Erik V.
    Cai, Lingchao
    ORGANIC LETTERS, 2023, 25 (17) : 2996 - 3000
  • [4] Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones
    Shu, Bing
    Song, Jia-Lin
    Chen, Shao-Yong
    Zheng, Yi-Chuan
    Zhang, Shang-Shi
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3499 - 3508
  • [5] Rh(III)-catalyzed C-H activation/intramolecular annulation for the synthesis of N-methoxydihydropyrimidin-2-one fused heterocycles
    Huang, Youchun
    Kang, Ke
    Zhong, Xiuwen
    Yu, Yongping
    Chen, Wenteng
    TETRAHEDRON LETTERS, 2023, 115
  • [6] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
    Cai, Libo
    Zhu, Xiaoyi
    Chen, Jiayi
    Lin, Aijun
    Yao, Hequan
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
  • [7] 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
  • [8] Rh(III)-catalyzed sequential C-H activation and annulation: access to N-fused heterocycles from arylazoles and α-diazocarbonyl compounds
    Jie, Jiyang
    Li, Haoyi
    Wu, Songxiao
    Chai, Qingyu
    Wang, Haining
    Yang, Xiaobo
    RSC ADVANCES, 2017, 7 (33) : 20548 - 20552
  • [9] Rh(III)-Catalyzed C-H Activation/Cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles
    Zhang, Yan
    Zheng, Jing
    Cui, Sunliang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14): : 6490 - 6500
  • [10] Rhodium(III)-Catalyzed C-H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds
    Barber, Joyann S.
    Kong, Dehuan
    Li, Wei
    McAlpine, Indrawan J.
    Nair, Sajiv K.
    Sakata, Sylvie K.
    Sun, Nicole
    Patman, Ryan L.
    SYNLETT, 2021, 32 (02) : 202 - 206
12345