Citation: Chen Cheng, Xu Mengmeng, Zhao Qing, Liu Chengxiu, Yang Hongjun, Feng Yuchuan. A Concisely Convergent Synthesis of Berberine Chloride[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 503-507. doi: 10.6023/cjoc201612005 shu

A Concisely Convergent Synthesis of Berberine Chloride

Chen Cheng ^a ,
Xu Mengmeng ^a ,
Zhao Qing ^b ,
Liu Chengxiu ^c ,
Yang Hongjun ^a,*,, ,
Feng Yuchuan ^a,*,,

a.
College of Chemistry & Environment Protection Engineering, Southwest University for Nationalities, Chengdu 610041
b.
Preparatory School, Southwest University for Nationalities, Chengdu 610041
c.
Southwest University for Nationalities Hospital, Chengdu 610041

Corresponding author: Yang Hongjun, yanghj@swun.cn Feng Yuchuan, yanghj@swun.cn
Received Date: 2 December 2016
Revised Date: 1 January 2017

Fund Project: the Research Projects Sichuan Provincial Department of Education 15ZB0487the Graduate Innovative Research Projects of Central Universities, Southwest University for Nationalities CX2015SZ045

Figures(4)

The berberine chloride was synthesized starting from benzo[d][1, 3]dioxole with the mild condition and the simple operation in overall 33% yield. The route includes the five steps of nucleophilic ring opening, deprotection and cyclization and so on. All intermediates were determined by ¹H NMR, ¹³C NMR and MS techniques.
- berberine chloride,
- convergent synthesis,
- benzo[d][1, 3]dioxole,
- grignard regent
1. [1]
  (a) Lo, C. Y.; Hsu, L. C.; Chen, M. S.; Lin, Y. J.; Chen, L. G.; Kuo, C. D.; Wu., J. Y. Bioorg. Med. Chem. Lett. 2013, 23, 305.
  (b) Li, Q.; Xiang, J. F.; Tang, Y. L. Chin. J. Chem. 2015, 33, 1041.
2. [2]
  Zhang, S. L.; Chang, J. J.; Damu, G. V.; Fang, B.; Zhou, X. D.; Geng, R. X.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2013, 23, 1008. doi: 10.1016/j.bmcl.2012.12.036
3. [3]
  (a) Samosorn, S.; Tanwirat, B.; Muhamad, N.; Casadei, G.; Tomkiewicz, D.; Lewis, K.; Suksamrarn, A.; Prammananan, T.; Gornall, K. C.; Beck, J. L.; Bremner, J. B. Bioorg. Med. Chem. 2009, 17, 3866.
  (b) Zhang, S. L.; Damu, G. L.; Zhang, L.; Geng, R. X.; Zhou, C. H. Eur. J. Med. Chem. 2012, 55, 164.
4. [4]
  Bodiwala, H. S.; Sabde, S.; Mitra, D.; Bhutani, K. K.; Singh, I. P. Eur. J. Med. Chem. 2011, 46, 1045. doi: 10.1016/j.ejmech.2011.01.016
5. [5]
  Vennerstrom, J. L.; Lovelace, J. K.; Wsits, V. B.; Hanson, W. L.; Klayman, D. L. Antimicrob. Agents Chemother. 1990, 34, 918. doi: 10.1128/AAC.34.5.918
6. [6]
  Bahar, M.; Deng, Y.; Zhu, X.; He, S.; Pandharkar, T.; Drew, M. E.; Navarro-Vazquez, A.; Anklin, C.; Gil, R. R.; Dos Kotch, R. W.; Werbovetz, K. A.; Kinghorn, A. D. Bioorg. Med. Chem. Lett. 2011, 21, 2606. doi: 10.1016/j.bmcl.2011.01.101
7. [7]
  (a) Letasiova, S.; Jantova, S.; Cipak, L.; Muckova, M. Cancer Lett. 2006, 239, 254.
  (b) Ma, Y.; Ou, T. M.; Tan, J. H.; Hou, J. Q.; Huang, S. L.; Gu, L. Q.; Huang, Z. S. Bioorg. Med. Chem. Lett. 2009, 19, 3414.
8. [8]
9. [9]
  (a) Roy, S. C.; Guin, C.; Rana, K. K.; Maiti, G. Tetrahedron Lett. 2001, 42, 6941.
  (b) Roy, S. C.; Guin, C.; Maiti, G. Tetrahedron Lett. 2001, 42, 9253.
10. [10]
  Tietze, L. F., Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264. doi: 10.1021/ja991650+
11. [11]
  Pan, J. F.; Yu, C.; Zhu, D. Y.; Zhang, H.; Ren, J. Y. CN 1314347, 2001 [Chem. Abstr. 2002, 137, 370266].
1. [1]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
2. [2]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
3. [3]
  Huicheng Yang , Qianhong Sun . Practice of Ideological and Political Education in Organic Chemistry Laboratory Courses under the OBE Framework: A Case Study of Berberine Extraction. University Chemistry, 2025, 40(5): 276-282. doi: 10.12461/PKU.DXHX202410091
4. [4]
  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
5. [5]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
6. [6]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
7. [7]
  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
8. [8]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
9. [9]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
10. [10]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
11. [11]
  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
12. [12]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
13. [13]
  Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . Facile synthesis of hierarchical Ti₃C₂/Bi₁₂O₁₇Br₂ Schottky heterojunction with photothermal effect for solar-driven antibiotics photodegradation. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-. doi: 10.1016/j.actphy.2025.100075
14. [14]
  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
15. [15]
  Weihua Jiang , Yongsheng Zhou , Qiaoqiao Teng . Progressive Teaching Model in the Practice and Exploration of Ideological and Political Education in Laboratory Courses: Taking the Organic Chemistry Experiment “Synthesis of Aspirin” as an Example. University Chemistry, 2024, 39(2): 99-104. doi: 10.3866/PKU.DXHX202306028
16. [16]
  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
17. [17]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
18. [18]
  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
19. [19]
  Zhenhua Wang , Haoyang Feng , Xiaoyang Shao , Wenru Fan . Vitamins in Solid Propellants: Controlled Synthesis of Neutral Macromolecular Bonding Agents. University Chemistry, 2025, 40(4): 1-9. doi: 10.3866/PKU.DXHX202401007
20. [20]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055

Get Citation

PDF

XML

Metrics

PDF Downloads(29)
Abstract views(2340)
HTML views(666)

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