One-Pot Synthesis of Polycyclic Spirooxindoles via Montmorillonite K10-Catalyzed C-H Functionalization of Cyclic Amines

被引:32
|
作者
Zhang, Xiaofeng [1 ,2 ]
Liu, Miao [1 ,2 ]
Qiu, Weiqi [1 ,2 ]
Evans, Jason [1 ,2 ]
Kaur, Manpreet [3 ]
Jasinski, Jerry P. [3 ]
Zhang, Wei [1 ,2 ]
机构
[1] Univ Massachusetts, Ctr Green Chem, 100 Morrissey Blvd, Boston, MA 02125 USA
[2] Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA
[3] Keene State Coll, Dept Chem, 229 Main St, Keene, NH 03435 USA
来源
关键词
3+2] Cycloaddition; Spirooxindoles; Montmorillonite K10; Heterogeneous catalysis; Recyclable; alpha-C-H functionalization; AZOMETHINE YLIDE ROUTE; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; 3+2 CYCLOADDITION; REDOX; CATALYSIS; OXINDOLES; TRANSFORMATIONS; STEREOCENTERS;
D O I
10.1021/acssuschemeng.8b00555
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for pot and atom economic synthesis of polycyclic spirooxindoles through alpha-C-H functionalization of cyclic amines has been developed. This highly efficient three-component [3+2] cycloaddition reaction was catalyzed by recyclable montmorillonite K10 and only water was produced as a byproduct.
引用
收藏
页码:5574 / 5579
页数:11
相关论文
共 50 条
  • [1] Phosphine-Catalyzed Remote β-C-H Functionalization of Amines Triggered by Trifluoromethylation of Alkenes: One-Pot Synthesis of Bistrifluoromethylated Enamides and Oxazoles
    Yu, Peng
    Zheng, Sheng-Cai
    Yang, Ning-Yuan
    Tan, Bin
    Liu, Xin-Yuan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 4041 - 4045
  • [2] One-Pot Synthesis of Amides from Aldehydes and Amines via C-H Bond Activation
    Cadoni, Roberta
    Porcheddu, Andrea
    Giacomelli, Giampaolo
    De Luca, Lidia
    [J]. ORGANIC LETTERS, 2012, 14 (19) : 5014 - 5017
  • [3] One-Pot Synthesis of Diarylmethylidenefluorenes and Phenanthrenes by Palladium-Catalyzed Multiple C-H Bond Functionalization
    Thirunavukkarasu, Vedhagiri S.
    Parthasarathy, Kanniyappan
    Cheng, Chien-Hong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1436 - 1440
  • [4] Ruthenium-catalyzed C-H bond functionalization in cascade and one-pot transformations
    Gramage-Doria, Rafael
    Bruneau, Christian
    [J]. COORDINATION CHEMISTRY REVIEWS, 2021, 428
  • [5] Copper-catalyzed one-pot synthesis of propargylamines via C-H activation in PEG
    Zhang, Qiang
    Chen, Jiu-Xi
    Gao, Wen-Xia
    Ding, Jin-Chang
    Wu, Hua-Yue
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (11) : 809 - 812
  • [6] Highly diastereoselective synthesis of polycyclic amines via redox neutral C-H functionalization
    Kumar, Chottanahalli S. Pavan
    Harsha, Kachigere B.
    Sandhya, Nagarakere C.
    Ramesha, Ajjalli B.
    Mantelingu, Kempegowda
    Rangappa, Kanchugarakoppal S.
    [J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (11) : 8397 - 8404
  • [7] Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins
    Hara, Yusuke
    Onodera, Shunsuke
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. ORGANIC LETTERS, 2015, 17 (19) : 4850 - 4853
  • [8] One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts
    Reitti, Marcus
    Villo, Piret
    Olofsson, Berit
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) : 8928 - 8932
  • [9] Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C-H Functionalization of Arenes
    Ghosh, Koushik
    Rit, Raja K.
    Ramesh, E.
    Sahoo, Akhila K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) : 7821 - 7825
  • [10] Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization
    Munnuri, Sailu
    Adebesin, Adeniyi Michael
    Paudyal, Mahesh P.
    Yousufuddin, Muhammed
    Dalipe, Alfonso
    Falck, John R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (50) : 18288 - 18294