A 2-(1-methylhydrazinyl)pyridine-directed C-H functionalization/spirocyclization cascade: facile access to spirosuccinimide derivatives

被引：53
|
作者：
Zhao, Hua [1 ]
Shao, Xiaoru [1 ]
Wang, Taimin [1 ]
Zhai, Shengxian [1 ,2 ]
Qiu, Shuxian [1 ]
Tao, Cheng [1 ,2 ]
Wang, Huifei [1 ]
Zhai, Hongbin [1 ,2 ,3 ]
机构：
[1] Peking Univ, Sch Chem Biol & Biotechnol, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 39期
关键词：
REMOVABLE DIRECTING GROUP; CARBON-HYDROGEN BONDS; UNACTIVATED C(SP(3))-H; AROMATIC AMIDES; BORONIC ACIDS; MALEIMIDES; ACTIVATION; CATALYSIS; ARYLATION; BENZAMIDES;
D O I：
10.1039/c8cc01774c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A cobalt-catalyzed oxidative coupling of benzoic hydrazides with maleimides by utilizing 2-(1-methylhydrazinyl)pyridine as a bidentate directing group has been developed. This C-H functionalization/spirocyclization cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous spirosuccinimides were obtained in good to excellent yields with high regioselectivity. This strategy also provides a novel and efficient access to diverse symmetric and unsymmetrical bisspirosuccinimides.
引用
收藏
页码：4927 / 4930
页数：4
相关论文
共 50 条
  • [31] Rh(iii)-Catalyzed switchable C-H monoalkenylation and dialkenylation of 2-(1H-pyrazol-1-yl)pyridine with alkenes via rollover cyclometalation
    Meng, Haifang
    Yang, Fang
    Chen, Mengjia
    Chen, Chen
    Zhu, Bolin
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (04) : 773 - 777
  • [32] Facile Synthesis of 2-(Phenylthio)phenols by Copper(I)-Catalyzed Tandem Transformation of C-S Coupling/C-H Functionalization (vol 132, pg 15531, 2010)
    Xu, Runsheng
    Wan, Jie-Ping
    Mao, Hui
    Pan, Yuanjiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (02) : 387 - 387
  • [33] Construction of Covalent Triazine Frameworks with Electronic Donor-Acceptor System for Efficient Photocatalytic C-H Hydroxylation of Imidazole[1,2-α]Pyridine Derivatives
    Qiao, Huijie
    Zhao, Kun
    Wang, Shixing
    Xu, Xiaoxu
    Chen, Sicheng
    Kong, Xiangtao
    Yang, Liting
    Jiao, Mingli
    Zhai, Lipeng
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (61)
  • [34] Rhodium(III)-catalyzed vinylic sp2 C-H bond functionalization: efficient synthesis of pyrido[1,2-α]benzimidazoles and imidazo[1,2-α]pyridines
    Dong, Lin
    Huang, Ji-Rong
    Qu, Chuan-Hua
    Zhang, Qian-Ru
    Zhang, Wei
    Han, Bo
    Peng, Cheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (36) : 6142 - 6149
  • [35] Rh(iii)-Catalyzed C(sp2)-H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives
    Han, Zhi-Peng
    Xu, Meng-Meng
    Zhang, Rui-Ying
    Xu, Xiao-Ping
    Ji, Shun-Jun
    GREEN CHEMISTRY, 2021, 23 (17) : 6337 - 6340
  • [36] Mono or double Pd-catalyzed C-H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives
    Ketata, Nahed
    Liu, Linhao
    Ben Salem, Ridha
    Doucet, Henri
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 427 - 435
  • [37] K2S2O8-mediated direct C-H functionalization to synthesize quinoxalin-2(1H)-one derivatives in water
    Qin, Hui
    Wei, Guo-Liang
    Zheng, Xiao-Wei
    Bao, Mei-Hua
    Zhang, Yi-Wen
    Huang, Ping
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (07) : 2945 - 2949
  • [38] Synthesis of 2-(fluorinated aryl)pyridine derivatives via palladium-catalyzed C-H bond arylation of fluorobenzenes using 2-halopyridines as aryl sources
    Boyaala, Rabab
    Touzani, Rachid
    Guerchais, Veronique
    Soule, Jean-Francois
    Doucet, Henri
    TETRAHEDRON LETTERS, 2017, 58 (33) : 3205 - 3208
  • [39] Facile synthesis of substituted 2-styrylnaphthyridine derivatives via sp3 C-H functionalization under mild conditions and their antimicrobial activity and Electrochemical properties
    Nampally, Umarani
    Satyanarayana, Neeli
    Bharathkumar, Hanumantharayappa
    Karingula, Sampath
    Anisetti, Ravindernath
    Banoji, Venkateswarlu
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1324
  • [40] An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via silver(I)-catalyzed C-H bond functionalization
    Mehdi Khoshneviszadeh
    Mehdi Soheilizad
    Maryam Fardpour
    Mohammad Mahdavi
    Monatshefte für Chemie - Chemical Monthly, 2017, 148 : 1817 - 1821
12345