Synthesis of 1H-Indole-2,3-dicarboxylates via Rhodium-Catalyzed C-H Annulation of Arylhydrazines with Maleates

被引:5
|
作者
Zhang, Sheng [1 ]
Li, He [2 ]
Yamamoto, Yoshinori [1 ,3 ]
Bao, Ming [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China
[2] Inner Mongolia Univ Nationalities, Coll Chem & Mat Sci, Tongliao 028000, Peoples R China
[3] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 19期
基金
中国国家自然科学基金;
关键词
INDOLE-2,3-DICARBOXYLIC ANHYDRIDES; BOND ACTIVATION; DIAZO-COMPOUNDS; FUNCTIONALIZATION; SYNTHONS;
D O I
10.1021/acs.joc.0c01727
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work describes a one-step synthesis of 1H-indole-2,3-dicarboxylates through C-H activation. Rhodium-catalyzed tandem C-H activation and annulation of 2-acetyl-1-phenylhydrazines with maleates proceeded smoothly in the presence of additive NaOAc and oxidant Ag2CO3 and produced the corresponding indole derivatives, 1H-indole-2,3-dicarboxylates, in satisfactory to good yields. A variety of useful functional groups were tolerated on the benzene ring including halogen atoms (F, Cl, Br, and I) and methoxycarbonyl groups.
引用
收藏
页码:12544 / 12552
页数:9
相关论文
共 50 条
  • [1] An efficient synthesis of isoquinolines via rhodium-catalyzed direct C-H functionalization of arylhydrazines
    Zhang, Sai
    Huang, Daorui
    Xu, Guangyang
    Cao, Shengyu
    Wang, Rong
    Peng, Shiyong
    Sun, Jiangtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (29) : 7920 - 7923
  • [2] Rhodium-catalyzed intramolecular annulation via C-H activation leading to fused tricyclic indole scaffolds
    Tao, Pengyu
    Jia, Yanxing
    CHEMICAL COMMUNICATIONS, 2014, 50 (55) : 7367 - 7370
  • [3] Electrochemical Rhodium-Catalyzed Enantioselective C-H Annulation with Alkynes
    Huang, Yuan-Qiong
    Wu, Zhi-Jie
    Zhu, Li
    Gu, Qing
    Lu, Xiaojie
    You, Shu-Li
    Mei, Tian-Sheng
    CCS CHEMISTRY, 2022, 4 (09): : 3181 - 3189
  • [4] Synthesis of Polyheteroaromatic Compounds via Rhodium-Catalyzed Multiple C-H Bond Activation and Oxidative Annulation
    Peng, Shiyong
    Liu, Suna
    Zhang, Sai
    Cao, Shengyu
    Sun, Jiangtao
    ORGANIC LETTERS, 2015, 17 (20) : 5032 - 5035
  • [5] Synthesis of Polysubstituted Phenols by Rhodium-Catalyzed C-H/Diazo Coupling and Tandem Annulation
    Liu, Min
    Yan, Kelu
    Wen, Jiangwei
    Li, Xue
    Wang, Xiaoyu
    Lu, Fengjie
    Wang, Xiu
    Wang, Hua
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) : 1855 - 1860
  • [6] Synthesis of Phthalides through Tandem Rhodium-Catalyzed C-H Olefination and Annulation of Benzamides
    Mishra, Neeraj Kumar
    Park, Jihye
    Choi, Miji
    Sharma, Satyasheel
    Jo, Hyeim
    Jeong, Taejoo
    Han, Sangil
    Kim, Saegun
    Kim, In Su
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (18) : 3076 - 3083
  • [7] Oxidative C-H/C-H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer
    Ghosh, Koushik
    Nishii, Yuji
    Miura, Masahiro
    ORGANIC LETTERS, 2020, 22 (09) : 3547 - 3550
  • [8] Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
    Yu, Shuling
    Hong, Chao
    Liu, Zhanxiang
    Zhang, Yuhong
    ORGANIC LETTERS, 2021, 23 (13) : 5054 - 5059
  • [9] Synthesis of Indole-Fused Polycyclics via Rhodium-Catalyzed Undirected C-H Activation/Alkene Insertion
    Guo, Songjin
    Pan, Rui
    Guan, Zhe
    Li, Panpan
    Cai, Libo
    Chen, Siwei
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2019, 21 (16) : 6320 - 6324
  • [10] Diastereoselective synthesis of tetrahydropyridines via rhodium-catalyzed C-H bond activation
    Lu, Colin
    Duttwyler, Simon
    Ellman, Jonathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244