Citation: Fu Chao, Fan Yanxia, Sun Qihui, Yi Weiyin, Yi Fengping. One-Pot Synthesis of 2-Benzyl-3, 4-dihydro-2H-isoquinolin-1-ones Catalyzed by CuCl₂[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 566-570. doi: 10.6023/cjoc201805024 shu

One-Pot Synthesis of 2-Benzyl-3, 4-dihydro-2H-isoquinolin-1-ones Catalyzed by CuCl₂

School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418

Corresponding author: Yi Fengping, yifengping@sit.edu.cn
Received Date: 10 May 2018
Revised Date: 24 July 2018
Available Online: 5 February 2018

Figures(1)

An facile, effective, copper-catalyzed one-pot approach to 2-benzyl-3, 4-dihydroquinolin-1-ones has been successfully developed. The compounds were achieved by the reaction of tetrahydroisoquinoline, benzyl azide and benzaldehyde in one-pot fashion via nucleophilic addition reaction followed by oxidation. The desired products were afforded in the high yield of 50%~70%. Moreover, The effects of different catalyst, additives, reaction temperature and proportion of substrates on the reaction were also investigated. The results showed that the optimizing conditions of reaction were CuCl₂ as catalyst, CH₃COOH as additive and toluene as solvent. A series of 2-benzyl-3, 4-dihydro-2H-isoquinolin-1-ones can be efficiently obtained under the optimizing conditions.
- CuCl₂,
- one-pot,
- 2-benzyl-3, 4-dihydro-2H-isoquinolin-1-ones
1. [1]
  (a) Siengalewicz, P.; Rinner, U.; Mulzer, J. Chem. Soc. Rev. 2008, 2676.
  (b) Campos, K. R.Chem. Soc. Rev. 2007, 36, 1069.
  (c) Lebold, T. P.; Wood, J. L.; Deitch, J.; Lodewyk, M. W.; Tantillo, D. J.; Sarpong, R. Nat. Chem. 2013, 5, 126.
  (d) Reddy, R. J.; Kawai, N.; Uenishi, J. J. Org. Chem. 2012, 77, 11101.
2. [2]
  Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. doi: 10.1021/cr010212u
3. [3]
  Chandrasekhar, S.; Mohanty, P. K. Org. Lett. 1999, 1, 877. doi: 10.1021/ol9901220
4. [4]
  Kashiwada, Y.; Aoshima, A.; Ikeshiro, Y. Bioorg. Med. Chem. 2005, 13, 443. doi: 10.1016/j.bmc.2004.10.020
5. [5]
  Zheng, M.; Zhang, X.; Zhao, M. Bioorg. Med. Chem. 2008, 16, 9574. doi: 10.1016/j.bmc.2008.09.019
6. [6]
  (a) Fisher, M. J.; Gunn, B. P.; Harms, C. S.; Kline, A. D.; Mullaney, J. T. Bioorg. Med. Chem. Lett. 1997, 7, 2537.
  (b) Jin, R.; Patureau, F. W. ChemCatChem 2015, 7, 223.
7. [7]
  (a) Gonzalez, D.; Martinot, T.; Hudlicky, T. Tetrahedron 1998, 40, 3077.
  (b) McNulty, J.; Mao, J.; Gibe, R.; Mo, R.; Wolf, S.; Pettit, G. R.; Herald, D. L.; Boyd, M. R. Bioorg. Med. Chem. Lett. 2011, 11, 169.
  (c) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockess, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995. 2551.
8. [8]
  Chern, M. S.; Li, W. R. Tetrahedron Lett. 2004, 45, 8323. doi: 10.1016/j.tetlet.2004.09.059
9. [9]
  Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684. doi: 10.1021/jo00403a013
10. [10]
  (a) So, M. H.; Liu, Y. L.; Ho, C. M.; Che, C. M. Chem. Asian J. 2009, 4, 1551.
  (b) Jin, X. J.; Kataoka, K.; Yatabe, T.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2016, 55, 7212.
11. [11]
  Khusnutdinova, J. R.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2014, 136, 2998. doi: 10.1021/ja500026m
12. [12]
  Griffiths, R.; Burly, G. A.; Talbot, E. P. A. Org. Lett. 2017, 19, 870. doi: 10.1021/acs.orglett.7b00021
13. [13]
  Sueda, T.; Kajishima, D.; Goto, S. J. Org. Chem. 2003, 58, 3307.
14. [14]
  Song, A. R.; Yu, J.; Zhang, C. Synthesis 2012, 44, 2903. doi: 10.1055/s-00000084
15. [15]
  Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Eur. J. Org. Chem. 2010, 1875.
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]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
3. [3]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
4. [4]
  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
5. [5]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
6. [6]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
7. [7]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
8. [8]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
9. [9]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-. doi: 10.1016/j.actphy.2025.100054
10. [10]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
11. [11]
  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
12. [12]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
13. [13]
  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
14. [14]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
15. [15]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
16. [16]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
17. [17]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
18. [18]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
19. [19]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
20. [20]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1069)
HTML views(173)

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

One-Pot Synthesis of 2-Benzyl-3, 4-dihydro-2H-isoquinolin-1-ones Catalyzed by CuCl2

Metrics

通讯作者: 陈斌, bchen63@163.com

One-Pot Synthesis of 2-Benzyl-3, 4-dihydro-2H-isoquinolin-1-ones Catalyzed by CuCl₂