The Cs2CO3-Catalyzed Reaction of 2-Oxindoles with Enones for the Preparation of Indolin-3-Ones and Their Further Transformation

被引:19
|
作者
Shao, Ying [1 ]
Zeng, Yu-Mei [1 ]
Ji, Jie-Ying [1 ]
Sun, Xiao-Qiang [1 ]
Yang, Hai-Tao [1 ]
Miao, Chun-Bao [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Adv Catalysis & Green Mfg Collaborat Innovat Ctr, Changzhou 213164, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 24期
基金
美国国家科学基金会;
关键词
CATALYZED INTRAMOLECULAR AMINATION; C-H AMINATION; INDOLE ALKALOIDS; SPIRO-PSEUDOINDOXYL; CASCADE; BONDS; (+)-ISATISINE; REARRANGEMENT; HYDROXYLATION; DERIVATIVES;
D O I
10.1021/acs.joc.6b01993
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Cs2CO3-catalyzed reaction of 2-oxindoles with enones affords 2,2-disubstituted indolin-3-ones through domino "Michael addition-oxidation-ring-cleavage-C-N coupling" process. O-2 acts as the sole oxidant to accomplish the oxidative process. The indolin-3-ones can be further transformed to pyridazine, azirdine-fused 3-oxindoles, 4-quinolone derivatives easily.
引用
收藏
页码:12443 / 12450
页数:8
相关论文
共 50 条
  • [31] Copper-Catalyzed Synthesis of C-2 Substituted Indolin-3-Ones and Indolin-3-One [4+2] Cycloadducts Through Azide-Tethered Iodonium Ylides
    Guerrero, Israel Najar
    Al-Khateeb, Zinah
    West, F. G.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [32] Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
    Zhang, Qing-Bao
    Jia, Wen-Liang
    Ban, Yong-Liang
    Zheng, Yong
    Liu, Qiang
    Wu, Li-Zhu
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (08) : 2595 - 2598
  • [33] Dearomative oxyphosphorylation of indoles enables facile access to 2,2-disubstituted indolin-3-ones
    Xiong, Ting
    Zhou, Xingcui
    Jiang, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (29) : 5721 - 5725
  • [34] Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction
    Xia, Zilei
    Hu, Jiadong
    Gao, Yu-Qi
    Yao, Qizheng
    Xie, Weiqing
    CHEMICAL COMMUNICATIONS, 2017, 53 (54) : 7485 - 7488
  • [35] Electrochemical Oxidative Addition of Nucleophiles on 2-Arylindoles: Synthesis of C2-Heteroquaternary Indolin-3-ones
    Nagare, Yadav Kacharu
    Shah, Imtiyaz Ahmad
    Yadav, Jyothi
    Pawar, Amol Prakash
    Rangan, Krishnan
    Choudhary, Rahul
    Iype, Eldhose
    Kumar, Indresh
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (23): : 15771 - 15782
  • [36] Ru-catalyzed oxidation and C-C bond formation of indoles for the synthesis of 2-indolyl indolin-3-ones under mild reaction conditions
    Zhou, Xiao-Yu
    Chen, Xia
    CANADIAN JOURNAL OF CHEMISTRY, 2020, 98 (11) : 667 - 669
  • [37] Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
    Liu, Yao-Zong
    Zhang, Jie
    Xu, Peng-Fei
    Luo, Yong-Chun
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7551 - 7555
  • [38] A multifunctionalized strategy of indoles to C2-quaternary indolin-3-ones via a TEMPO/Pd-catalyzed cascade process
    Deng, Zhongfu
    Peng, Xiangjun
    Huang, Panpan
    Jiang, Lili
    Ye, Dongnai
    Liu, Liangxian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (02) : 442 - 448
  • [39] Cs2CO3-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes
    Song, Song
    Zhang, Yiqun
    Yeerlan, Adeli
    Zhu, Bencong
    Liu, Jianzhong
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2487 - 2491
  • [40] Thermal and acid-catalyzed Hofmann-Martius rearrangement of 3-N-aryl-2-oxindoles into 3-(arylamino)-2-oxindoles
    Magnus, Philip
    Turnbull, Rachel
    ORGANIC LETTERS, 2006, 8 (16) : 3497 - 3499