Citation: Jie Zhou, Bai Ling Xu. Three-component one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives in hexafluoroisopropanol[J]. Chinese Chemical Letters, ;2008, 19(8): 921-924. doi: 10.1016/j.cclet.2008.05.008 shu

Three-component one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives in hexafluoroisopropanol

Jie Zhou ,
Bai Ling Xu

Institute of Materia. Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Belting 100050, China

Received Date: 25 March 2008

Fund Project: We thank the National Natural Science Foundation of China (No.30672540) and NSF of Beijing (No.7072048) for financial support

The one-pot aza-Diels-Alder reaction of substituted aromatic amines, ethyl glyoxylate and benzyl vinylcarbamate or N-benzyloxycarbonyl 2-pyrroline was conducted in hexafluoroisopropanol, providing the desired 1,2,3,4-tetrahydroquinline derivatives in moderate yields.
- Aza-Diels-Alder reaction,
- Tetrahydroquinoline,
- Hexafluoroisopropanol (HFIP),
- Fluorinated solvent
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
3. [3]
  Dong-Sheng Deng , Su-Qin Tang , Yong-Tu Yuan , Ding-Xiong Xie , Zhi-Yuan Zhu , Yue-Mei Huang , Yun-Lin Liu . C-F insertion reaction sheds new light on the construction of fluorinated compounds. Chinese Chemical Letters, 2024, 35(8): 109417-. doi: 10.1016/j.cclet.2023.109417
4. [4]
  Jiayu Xu , Meng Li , Baoxia Dong , Ligang Feng . Fully fluorinated hybrid zeolite imidazole/Prussian blue analogs with combined advantages for efficient oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(6): 108798-. doi: 10.1016/j.cclet.2023.108798
5. [5]
  Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2024.100199
6. [6]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
7. [7]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
8. [8]
  Jun-Ting Mo , Zheng Wang . Achieving tunable long persistent luminescence in metal organic halides based on pyridine solvent. Chinese Chemical Letters, 2024, 35(9): 109360-. doi: 10.1016/j.cclet.2023.109360
9. [9]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
10. [10]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
11. [11]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
12. [12]
  Lan Yang , Yu Li , Mou Jiang , Rui Zhou , Hengjiang Cong , Minghui Yang , Lei Zhang , Shenhui Li , Yunhuang Yang , Maili Liu , Xin Zhou , Zhong-Xing Jiang , Shizhen Chen . Fluorinated [2]rotaxanes as sensitive ¹⁹F MRI agents: Threading for higher sensitivity. Chinese Chemical Letters, 2024, 35(10): 109512-. doi: 10.1016/j.cclet.2024.109512
13. [13]
  Jianwen Zhao , Shuai Wang , Shanshan Zhao , Liwei Chen , Fangang Meng , Xuelin Tian . A non-fluorinated liquid-like membrane with excellent anti-scaling performance for membrane distillation. Chinese Chemical Letters, 2025, 36(1): 109883-. doi: 10.1016/j.cclet.2024.109883
14. [14]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
15. [15]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
16. [16]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
17. [17]
  Lulu Cao , Yikun Li , Dongxiang Zhang , Shuai Yue , Rong Shang , Xin-Dong Jiang , Jianjun Du . Engineering aggregates of julolidine-substituted aza-BODIPY nanoparticles for NIR-II photothermal therapy. Chinese Chemical Letters, 2024, 35(12): 109735-. doi: 10.1016/j.cclet.2024.109735
18. [18]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
19. [19]
  Yan Zhu , Jia Liu , Meiheng Lv , Tingting Wang , Dongxiang Zhang , Rong Shang , Xin-Dong Jiang , Jianjun Du , Guiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
20. [20]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(501)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return