Home

Citation: Jianping Fu, Wei Xiong, Juwu Hu, Xiaodan Han. Study on the Efficient Synthesis of Quinoline Derivatives from Cyclobutenones[J]. Chemistry, ;2021, 84(2): 178-181. shu

Study on the Efficient Synthesis of Quinoline Derivatives from Cyclobutenones

Institute of Applied Chemistry, Jiangxi Academy of Sciences, Nanchang, 330096

Corresponding author: Xiaodan Han, fjpxys@126.com
Received Date: 17 July 2020
Accepted Date: 27 September 2020

Figures(3)

A series of quinoline derivatives were successfully obtained through opening-cyclization reaction of 3-amino-2-cyclobutanones in the presence of acid. By screening the reaction solvent, catalyst, temperature, feed ratio and other factors, the optimal reaction conditions were obtained. The method exhibits many advantages such as low temperature, high yield, rapid response and so on, and it establishes a simple and effective new method for the synthesis of quinoline derivatives.
- Cyclobutanones,
- Ring opening reaction,
- Quinoline
1. [1]
  Yan X, Hu X. J. Org. Chem., 2014, 79(11): 5282~5286.
2. [2]
  Harrowven D C, Pascoe D D, Guy I L. Angew. Chem., 2007, 119(3): 429~432.
3. [3]
  Harrowven D C, Mohamed M, Goncalves T P, et al. Angew. Chem. Int. Ed., 2012, 51(18): 4405~4408.
4. [4]
  Chen P H, Siebe J, Senanayake C H, et al. Chem. Sci., 2015, 6(10): 5440~5445.
5. [5]
  Chen P H, Dong G. Chem. Eur. J., 2016, 22(51): 18290~18315.
6. [6]
  Xu S L, Moore H W. J. Org. Chem., 1992, 57(1): 326~338.
7. [7]
  Liebeskind L S, Iyer S, Jewel C F. J. Org. Chem., 1986, 51(15): 3065~3067.
8. [8]
  Kondo T, Taguchi Y, Kaneko Y, et al. Angew. Chem. Int. Ed., 2004, 43(40): 5369~5372.
9. [9]
  Liebeskind L S, Wang J Y. Tetrahedron, 1993, 49(25): 5461~5470.
10. [10]
  Huffman M A, Liebeskind L S. J. Am. Chem. Soc., 1993, 115(11): 4895~4896.
11. [11]
  Zhao Y L, Yang S C, Di C H, et al. Chem. Commun., 2010, 46: 7614~7616.
12. [12]
  Han X D, Zhao Y L, Meng J, et al. J. Org. Chem., 2012, 77(11): 5173~5178.
13. [13]
  Han X D, Fu J P, Hu J W, et al. Tetrahed. Lett., 2019, 60(49): 151304.
14. [14]
  Mitscher L. Chem. Rev., 2005, 105(2): 559~592.
15. [15]
  Chackal S, Houssin R, Hénichart J. J. Org. Chem., 2002, 67(10): 3502~3505.
16. [16]
  Zhao Y L, Yang S C, Di C H, et al. Chem. Commun., 2010, 46(40): 7614~7616.
17. [17]
1. [1]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
2. [2]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
3. [3]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
4. [4]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
5. [5]
  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
6. [6]
  Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
7. [7]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
8. [8]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
9. [9]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
10. [10]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
11. [11]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
12. [12]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
13. [13]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
14. [14]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
15. [15]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
16. [16]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
17. [17]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
18. [18]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
19. [19]
  Yuan Chun , Lijun Yang , Jinyue Yang , Wei Gao . Ideological and Political Design of BZ Oscillatory Reaction Experiment. University Chemistry, 2024, 39(2): 72-76. doi: 10.3866/PKU.DXHX202308072
20. [20]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(376)
HTML views(105)

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