Citation: Dai Hongguang, Liu Xuhui, Wang Lirong, Shi Lan. Synthesis of N-Substituted Pyrroles using Lignosulfonic Acid as Biomass-Based Catalyst[J]. Chemistry, ;2018, 81(10): 929-933. shu

Synthesis of N-Substituted Pyrroles using Lignosulfonic Acid as Biomass-Based Catalyst

College of Science, Inner Mongolia Agricultural University, Hohhot 010018

Corresponding author: Dai Hongguang, imaudm@imau.edu.cn
Received Date: 18 May 2018
Accepted Date: 29 July 2018

Figures(4)

Lignosulfonic acid is a kind of heterogeneous, environmentally friendly, biomass-based solid catalyst. In this paper, it was prepared by ion-exchange method using sodium lignosulfonate in papermaking waste as raw material. Its structure was characterized by FT-IR, elemental analysis and titration. Using lignosulfonic acid as a catalyst, N-substituted pyrroles were synthesized efficiently by Paal-Knorr reaction of hexane-2, 5-dione and primary amine in good to excellent yields. This is a typical nucleophilic reaction. The stronger the nucleophilic ability of the primary amine, the more easily the reaction proceeds.
- Paal-Knorr reaction,
- Lignosulfonic acid,
- Pyrroles,
- Biomass-based catalyst
1. [1]
  Y H He, G Q Wang, G Zhi. J. Heterocycl. Chem., 2010, 47(2): 486~489.
2. [2]
  L Ackermann, L T Kaspar, C J Gschrei. Chem. Commun., 2004, (24): 2824~2825.
3. [3]
  A Alberola, A G Ortega, M L Sadaba. Tetrahedron, 1999, 55(21): 6555~6566.
4. [4]
  R Ballini, L Barboni, G Bosica et al. Synlett, 2000, (3): 391~393.
5. [5]
  R Sreekumar, R Padmakumar. Synth. Commun., 1998, 28(9): 1661~1665.
6. [6]
  F Texier-Boullet, B Klein, J Hamelin. Synthesis-Stuttgart, 1986, (5): 409~411.
7. [7]
  M Kidwai, K Singhal, S Rastogi. J. Heterocycl. Chem., 2006, 43(5): 1231~1236.
8. [8]
  C Y Chen, X Y Guo, G Q Lu et al. New Carbon Mater., 2017, 32(2): 160~167.
9. [9]
  B K Banik, I Banik, M Renteriaa. Tetrahed. Lett., 2005, 46(15): 2643~2645.
10. [10]
  J Y Chen, H Y Wu, Z G Zheng et al. Tetrahed. Lett., 2006, 47(30): 5383~5387.
11. [11]
  M Curini, F Montanari, O Rosati et al. Tetrahed. Lett., 2003, 44(20): 3923~3925.
12. [12]
  J X Chen, M C Liu, X L Yang et al. J. Braz. Chem. Soc., 2008, 19(5): 877~883.
13. [13]
  P Armugam, P T Perumal. Chem. Lett., 2006, 35(6): 632~633.
14. [14]
  D Akbaslar, O Demirkol, S Giray. Synth. Commun., 2014, 44(9): 1323~1332.
15. [15]
  B K Banik, S Samajdar, I Bnik. J. Org. Chem., 2004, 69(1): 213~216.
16. [16]
  B Wang, Y Gu, C Luo et al. Tetrahed. Lett., 2004, 45(17): 3417~3419.
17. [17]
  L Akelis, J Rousseau, R Juskenas et al. Eur. J. Org. Chem., 2016, (1): 31~35.
18. [18]
  K Aghapoor, F Mohsenzadeh, H R Darabi et al. Res. Chem. Intermed., 2016, 42(2): 407~415.
19. [19]
  H T Luo, Y R Kang, Q Li et al. Heteroatom. Chem., 2008, 19(2): 144~148.
20. [20]
  D J Shaw, W F Wood. J. Chem. Educ., 1992, 69(12): A313.
21. [21]
  S Raghavan, K Anuradha. Synlett, 2003, (5): 711~713.
22. [22]
  X H Zhu, G Chen, Z L Xu et al. Chin. J. Org. Chem., 2008, 28(1): 115~119.
23. [23]
  H Veisi, P Mohammadi, J Gholami. Appl. Organomet. Chem., 2014, 28(12): 868~873.
24. [24]
  A J Abbas, A Sakineh, T Fatemah. J. Appl. Polym. Sci., 2012, 125(2): 1339~1345.
25. [25]
  A Najmadin, D Anahita, E Farshid et al. Monats. Chem., 2013, 144(3): 405~409.
26. [26]
  R Ali. React. Funct. Polym., 2011, 71(1): 80~83.
27. [27]
28. [28]
  J X Chen, X L Yang, M C Liu et al. Synth. Commun., 2009, 39(23): 4180~4198.
29. [29]
  B K Banik, S Samajdar, I Banik. J. Org. Chem., 2004, 69(1): 213~216.
30. [30]
  S K KPasha, V S V Satyanarayana, A S Kumar et al. Chin. Chem. Lett., 2011, 22(8): 891~894.
31. [31]
  D G Hulcoop, M Lautens. Org. Lett., 2007, 9(9): 1761~1764.
1. [1]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
2. [2]
  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.2023.100199
3. [3]
  Xuan Liu , Qing Li . Tailoring interatomic active sites for highly selective electrocatalytic biomass conversion reaction. Chinese Chemical Letters, 2025, 36(4): 110670-. doi: 10.1016/j.cclet.2024.110670
4. [4]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
5. [5]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
6. [6]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
7. [7]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
8. [8]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
9. [9]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
10. [10]
  Di Wang , Qing-Song Chen , Yi-Ran Lin , Yun-Xin Hou , Wei Han , Juan Yang , Xin Li , Zhen-Hai Wen . Tuning strategies and electrolyzer design for Bi-based nanomaterials towards efficient CO2 reduction to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(8): 100346-100346. doi: 10.1016/j.cjsc.2024.100346
11. [11]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
12. [12]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
13. [13]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
14. [14]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
15. [15]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
16. [16]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
17. [17]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
18. [18]
  Xiaoru LIU , Jinlian SHI , Yajia ZHENG , Shuangcun MO , Zhongxuan XU . Two Ni-based frameworks with helices and dinuclear units constructed from semi-rigid carboxylic acid and imidazole derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 797-808. doi: 10.11862/CJIC.20240328
19. [19]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
20. [20]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(210)
HTML views(15)

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