Citation:
Alireza Asghari, Mohsen Ameri, Ali Akbar Ziarati, Sepideh Radmannia, Ali Amoozadeh, Behruz Barfi, Leila Boutorabi. Electro-oxidation of paracetamol in the presence of malononitrile: Application for green, efficient, none-catalyst, simple and one-pot electro-synthesis of new paracetamols[J]. Chinese Chemical Letters,
;2015, 26(6): 681-684.
doi:
10.1016/j.cclet.2015.03.036
-
Electrochemical oxidation of paracetamol has been studied in the presence of malononitrile as a nucleophile in a phosphate buffer solution (0.15 mol/L, pH 7), using cyclic voltammetric techniques. The results indicated that the N-acetyl-p-benzoquinone-imine derived from paracetamol participates in a 1,4-Michael-type addition reaction with the malononitrile to form the corresponding paracetamol derivatives (6a, 7a). The present study has led to the development of a simple, green, non-catalyst and one-pot electrochemical method with high atom economy under mild conditions.
-
-
-
[1]
[1] W.T. Beaver, D. McMillian, Methodological considerations in the evaluation of analgesic combinations: acetaminophen (paracetamol) and hydrocodone in postpartum pain, Br. J. Clin. Pharmacol. 10 (Suppl. 2) (1980) 215S-223S.
-
[2]
[2] D.R. Mehlisch, The efficacy of combination analgesic therapy in relieving dental pain, J. Am. Dent. Assoc. 133 (2002) 861-871.
-
[3]
[3] R.M. Botting, Mechanism of action of acetaminophen: is there a cyclooxygenase 3? Clin. Infect. Dis. 31 (2000) S202-S210.
-
[4]
[4] R.V. Blanke, W.J. Decker, in: N.W. Tietz (Ed.), Textbook of Clinical Chemistry, W.B. Saunders, Philadelphia, 1986.
-
[5]
[5] D. Gunnell, V. Murray, K. Hawton, Use of paracetamol (acetaminophen) for suicide and nonfatal poisoning: worldwide patterns of use and misuse, Suicide Life Threat. Behav. 30 (2000) 313-326.
-
[6]
[6] N. Wangfuengkanagul, O. Chailapakul, Electrochemical analysis of acetaminophen using a boron-doped diamond thin film electrode applied to flow injection system, J. Pharm. Biomed. Anal. 28 (2002) 841-847.
-
[7]
[7] D. Nematollahi, S. Momeni, S. Khazalpour, A green electrochemical method for the synthesis of acetaminophen derivatives, J. Electrochem. Soc. 161 (2014) H75-H78.
-
[8]
[8] A. Amani, S. Khazalpour, D. Nematollahi, Electrochemical oxidation of acetaminophen and 4-(piperazin-1-yl) phenols in the presence of 4-hydroxy-1-methyl-2 (1H)-quinolone, J. Electrochem. Soc. 160 (2013) H33-H40.
-
[9]
[9] E. Tammari, M. Kazemi, A. Amani, Electrochemical oxidation of acetaminophen in the presence of barbituric acid derivatives, J. Electrochem. Soc. 161 (2014) G69-G73.
-
[10]
[10] M. Ameri, A. Asghari, A. Amoozadeh, M. Bakherad, D. Nematollahi, Green and highly efficient synthesis of new bis-benzofurans via electrochemical methods under ECECCC mechanism, J. Electrochem. Soc. 161 (2014) G75-G80.
-
[11]
[11] M. Ameri, A. Asghari, A. Amoozadeh, M. Bakherad, D. Nematollahi, Facile and onepot, electro-organic synthesis of a new bis-quinone by the ECCE mechanism in green media, Chin, Chem. Lett. 25 (2014) 1607-1610.
-
[12]
[12] D. Nematollahi, R.A. Rahchamani, Electrochemical synthesis of p-tolylsulfonylbenzenediols, Tetrahedron. Lett. 43 (2002) 147-150.
-
[13]
[13] D. Nematollahi, R.A. Rahchamani, Electro-oxidation of catechols in the presence of benzenesulfinic acid. Application to electro-organic synthesis of new sulfone derivatives, J. Electroanal. Chem. 520 (2002) 145-149.
-
[14]
[14] D. Nematollahi, H. Shayani-Jam, M. Alimoradi, S. Niroomand, Electrochemical oxidation of acetaminophen in aqueous solutions: kinetic evaluation of hydrolysis, hydroxylation and dimerization processes, Electrochim. Acta 54 (2009) 7407-7415.
-
[1]
-
-
-
[1]
Yifen He , Chao Qu , Na Ren , Dawei Liang . Enhanced degradation of refractory organics in ORR-EO system with a blue TiO2 nanotube array modified Ti-based Ni-Sb co-doped SnO2 anode. Chinese Chemical Letters, 2024, 35(8): 109262-. doi: 10.1016/j.cclet.2023.109262
-
[2]
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
-
[3]
Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
-
[4]
Xiaomei Ning , Liang Zhan , Xiaosong Zhou , Jin Luo , Xunfu Zhou , Cuifen Luo . Preparation and Electro-Oxidation Performance of PtBi Supported on Carbon Cloth: A Recommended Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 217-224. doi: 10.3866/PKU.DXHX202401085
-
[5]
Hao WANG , Kun TANG , Jiangyang SHAO , Kezhi WANG , Yuwu ZHONG . Electro-copolymerized film of ruthenium catalyst and redox mediator for electrocatalytic water oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2193-2202. doi: 10.11862/CJIC.20240176
-
[6]
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
-
[7]
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
-
[8]
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
-
[9]
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
-
[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]
Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
-
[12]
Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn0.8Fe0.2PO4 by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
-
[13]
Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
-
[14]
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
-
[15]
Fenglin Jiang , Anan Liu , Qian Wei , Youcai Hu . Editing function of type Ⅱ thioesterases in the biosynthesis of fungal polyketides. Chinese Chemical Letters, 2024, 35(10): 109504-. doi: 10.1016/j.cclet.2024.109504
-
[16]
Wenjing Dai , Lan Luo , Zhen Yin . Interface reconstruction of hybrid oxide electrocatalysts for seawater oxidation. Chinese Journal of Structural Chemistry, 2025, 44(3): 100442-100442. doi: 10.1016/j.cjsc.2024.100442
-
[17]
Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
-
[18]
Ajay Piriya Vijaya Kumar Saroja , Yuhan Wu , Yang Xu . Improving the electrocatalysts for conversion-type anodes of alkali-ion batteries. Chinese Journal of Structural Chemistry, 2025, 44(1): 100408-100408. doi: 10.1016/j.cjsc.2024.100408
-
[19]
Lu-Lu He , Lan-Tu Xiong , Xin Wang , Yu-Zhen Li , Jia-Bao Li , Yu Shi , Xin Deng , Zi-Ning Cui . Application of inhibitors targeting the type III secretion system in phytopathogenic bacteria. Chinese Chemical Letters, 2025, 36(4): 110044-. doi: 10.1016/j.cclet.2024.110044
-
[20]
Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H4PMo11VO40 catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(768)
- HTML views(1)