Citation:
Mohsen Ameri, Alireza Asghari, Ali Amoozadeh, Mohammad Bakherad, Davood Nematollahi. Facile and one-pot, electro-organic synthesis of a new bis-quinone by the ECCE mechanism in green media[J]. Chinese Chemical Letters,
;2014, 25(12): 1607-1610.
doi:
10.1016/j.cclet.2014.06.022
-
Electrochemical oxidation of 4-methyl catechol (1a) is investigated in the presence of 1,3-indandione (3) as nucleophile in phosphate buffer solution (0.2 mol/L, pH 6) mixed with ethanol as organic green solvent (50/50) using cyclic voltammetry and controlled-potential coulometry. The results indicated that quinones derived from electro-oxidation of 1a, participated in a 1,4-Michael addition reaction with 1,3-indandione (3) under ECCEmechanism. In this direction, a new bis-quinone was synthesized in high yield and good purity using a facile and convenient electrochemical pathway by carbon anode electrodes in an undivided cell.
-
-
-
[1]
[1] S. Patai, The Chemistry of the Quinonoid Compounds Part 1 and 2, John Wiley & Sons, New York, 1974.
-
[2]
[2] L.F. Fieser, M. Fieser, Organic Chemistry, 3rd ed., D.C. Heath and Company, Boston, 1956.
-
[3]
[3] T. Komiyama, T. Kikuchi, Y. Sugiura, Interactions of anticancer quinone drugs, aclacinomycin A, adriamycin, carbazilquinone, and mitomycin C, with NADPHcytochrome P-450 reductase, xanthine oxidase and oxygen, J. Pharmacobio-Dyn. 9 (1986) 651-664.
-
[4]
[4] D. Nematollahi, M. Hesari, Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives, J. Electroanal. Chem. 577 (2005) 197-203.
-
[5]
[5] D. Nematollahi, S. Khazalpour, A. Amani, Electrochemical oxidation of 4-(piperazin-1-yl)phenol in the presence of aryl sulfinic acids, J. Electrochem. Soc. 159 (2012) E82-E86.
-
[6]
[6] 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.
-
[7]
[7] D. Nematollahi, A. Amani, E. Tammari, Electrosynthesis of symmetric and highly conjugated benzofuran via a unique ECECCC electrochemical mechanism: evidence for predominance of electrochemical oxidation versus intramolecular cyclization, J. Org. Chem. 72 (2007) 3646-3651.
-
[8]
[8] L. Fotouhi, M. Khakpour, D. Nematollahi, M.M. Heravi, Investigation of the electrochemical behavior of some catechols in the presence of 4,6-dimethylpyrimidine-2-thiol, ARKIVOC (ii) (2008) 43-52.
-
[9]
[9] T.E. Young, J.R. Griswold, M.H. Hulbert, I. Melanin, Kinetics of the oxidative cyclization of dopa to dopaquinone, J. Org. Chem. 39 (1974) 1980-1982.
-
[10]
[10] M.D. Ryan, A. Yueh, W.Y. Chen, The electrochemical oxidation of substituted catechols, J. Electrochem. Soc. 127 (1980) 1489-1495.
-
[11]
[11] D. Habibi, D. Nematollahi, Z. Seyyed Al-Hoseini, S. Dehdashtian, A facile galvanostatic method for the synthesis of quinoxalinediones, Electrochim. Acta 52 (2006) 1234-1239.
-
[12]
[12] M. Ameri, A. Asghari, A. Amoozadeh, H. Daneshinejad, D. Nematollahi, Electrosynthesis of hydroquinonethioethers using electrochemical oxidation of hydroquinone in the presence of thiouracil derivatives, Chin. Chem. Lett. 25 (2014) 797-801.
-
[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]
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
-
[3]
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
-
[4]
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
-
[5]
Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP2/C anode with native oxidation POx component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
-
[6]
Qinwen Zheng , Xin Liu , Lintao Tian , Yi Zhou , Libing Liao , Guocheng Lv . Mechanism of Fenton catalytic degradation of Rhodamine B induced by microwave and Fe3O4. Chinese Chemical Letters, 2025, 36(4): 109771-. doi: 10.1016/j.cclet.2024.109771
-
[7]
Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
-
[8]
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
-
[9]
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
-
[10]
Yu Yao , Jinqiang Zhang , Yantao Wang , Kunsheng Hu , Yangyang Yang , Zhongshuai Zhu , Shuang Zhong , Huayang Zhang , Shaobin Wang , Xiaoguang Duan . Nitrogen-rich carbon for catalytic activation of peroxymonosulfate towards green synthesis. Chinese Chemical Letters, 2024, 35(11): 109633-. doi: 10.1016/j.cclet.2024.109633
-
[11]
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
-
[12]
Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
-
[13]
Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C3N4 for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
-
[14]
Jun-Ting Mo , Zheng Wang . Achieving tunable long persistent luminescence in metal organic halides based on pyridine solvent. Chinese Chemical Letters, 2024, 35(9): 109360-. doi: 10.1016/j.cclet.2023.109360
-
[15]
Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
-
[16]
Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
-
[17]
Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Boosting bulk charge transport of CuWO4 photoanodes via Cs doping for solar water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100207-100207. doi: 10.1016/j.cjsc.2023.100207
-
[18]
Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
-
[19]
Rui Cheng , Tingting Zhang , Xin Huang , Jian Yu . Facile synthesis of high-brightness green-emitting carbon dots with narrow bandwidth towards backlight display. Chinese Chemical Letters, 2024, 35(5): 108763-. doi: 10.1016/j.cclet.2023.108763
-
[20]
Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(590)
- HTML views(0)