Citation: Rahul R. NAGAWADE, Devanand B. SHINDE. Zirconyl Chloride Promoted Highly Efficient Domino Synthesis of New 1, 2, 3, 4-Tetrahydroquinoline Derivatives in Water[J]. Chinese Chemical Letters, ;2006, 17(9): 1137-1140. shu

Zirconyl Chloride Promoted Highly Efficient Domino Synthesis of New 1, 2, 3, 4-Tetrahydroquinoline Derivatives in Water

Rahul R. NAGAWADE ^1,2, ,
Devanand B. SHINDE ²

1.
Division of Medicinal Chemistry-New Drug Discovery, Wockhardt Research Centre, Aurangabad-431210(M. S.), India;Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004(M. S.), India;
2.
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004(M. S.), India

Received Date: 9 March 2006

The tetrahydroquinoline moiety is a structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers catalyzed by zirconyl chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclized products showed cis selectivity. The cis selectivity was tentatively rationalized due to chelation control in water.
- Anilines,
- cyclic enol ether,
- domino reaction,
- tetrahydroquinoline,
- zirconyl chloride
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Quanxing Mao , Zhengliang Wang , Zhinan Hu , Ziqi Yang , Hui Li , Yali Yao , Zijun Yong , Tianyi Ma . Facial detection of formaldehyde by using acidichromic carbon dots and the reaction between formaldehyde and ammonium chloride. Chinese Chemical Letters, 2025, 36(7): 110499-. doi: 10.1016/j.cclet.2024.110499
3. [3]
  Fangqing Zhang , Yu Wang , Zhenda Tan , Yangbin Liu , Lijuan Song , Xiaoming Feng . Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers. Chinese Chemical Letters, 2025, 36(7): 110581-. doi: 10.1016/j.cclet.2024.110581
4. [4]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
5. [5]
  Xinyu Hu , Bo Song , Shukai Song , Qinghui Ling , Bangkun Yue , Lianrui Hu , Feifei Wang , Li He , Lin Xu . Development of luminescent metallohelicate as a selective chloride transporter. Chinese Chemical Letters, 2025, 36(12): 110918-. doi: 10.1016/j.cclet.2025.110918
6. [6]
  Kailong Zhang , Chao Zhang , Luanhui Wu , Qidong Yang , Jiadong Zhang , Guang Hu , Liang Song , Gaoran Li , Wenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618
7. [7]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
8. [8]
  Wu-Jian Long , Yang Yu , Chuang He . A novel and promising engineering application of carbon dots: Enhancing the chloride binding performance of cement. Chinese Chemical Letters, 2024, 35(6): 108943-. doi: 10.1016/j.cclet.2023.108943
9. [9]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425
10. [10]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
11. [11]
  Jinhui Xu , Yanting Zhang , Kecheng Wen , Xinyu Wang , Zhiwei Yang , Yuan Huang , Guozhong Zheng , Lupeng Huang , Jing Zhang . Enhanced removal of polystyrene nanoplastics by air flotation modified by dodecyltrimethylammonium chloride: Performance and mechanism. Chinese Chemical Letters, 2025, 36(5): 110240-. doi: 10.1016/j.cclet.2024.110240
12. [12]
  Hai-Ying Yu , Yu-Wei Huang , Li-Ping Lin , Ren-Xiang Tan . Unprecedented diphenyl ether hybrids and spiro-diphenyl ether with antioxidant activity from Aspergillus sp. F1-8A associated with toad venom. Chinese Chemical Letters, 2026, 37(2): 111121-. doi: 10.1016/j.cclet.2025.111121
13. [13]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
14. [14]
  Xiao Zhu , Yanbing Mo , Jiawei Chen , Gaopan Liu , Yonggang Wang , Xiaoli Dong . A weakly-solvated ether-based electrolyte for fast-charging graphite anode. Chinese Chemical Letters, 2024, 35(8): 109146-. doi: 10.1016/j.cclet.2023.109146
15. [15]
  Xinzhe ZHANG , Jiarong XU , Mochou GAO , Yage LIU , Yanbao ZHAO , Jingzeng CUI , Xueyan ZOU . Silver chloride/chitosan-based chloramine nanohybrid with excellent antibacterial activity: Design and structure characterization as well as Ag⁺-Cl^- synergistic antibacterial effect. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 428-438. doi: 10.11862/CJIC.20250123
16. [16]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
17. [17]
  Yu-Chen Fang , Jia-He Chen , Mi-Zhuan Li , Hui-Min Li , Mei Bai , Yong-Zheng Chen , Zi-Wei Gao , Wen-Yong Han . Forging of silaoxycarbocyclics by interrupted Catellani reaction. Chinese Chemical Letters, 2025, 36(7): 110474-. doi: 10.1016/j.cclet.2024.110474
18. [18]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
19. [19]
  Feng Zhao , Hongyu Ding , Ting Sun , Chao Shen , Zu-Li Wang , Wei Wei , Dong Yi . Visible-light-promoted multi-component carbene transfer reactions of diazo compounds via ring-opening of cyclic ethers. Chinese Chemical Letters, 2026, 37(2): 111834-. doi: 10.1016/j.cclet.2025.111834
20. [20]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1375)
HTML views(30)

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