Citation:
Davood Nematollahi, Saied Saeed Hosseiny Davarani, Pari Mirahmadpour, Fahimeh Varmaghani. A facile electrochemical method for the synthesis of new sulfonamide derivatives of potential biological significance[J]. Chinese Chemical Letters,
;2014, 25(4): 593-595.
doi:
10.1016/j.cclet.2014.01.005
-
The electrochemical synthesis of some new sulfonamide derivatives was carried out via the electrochemical oxidation of 2,3-dihydrophthalazine-1,4-dione (1) in the presence of arylsulfinic acids (2a and 2b) as nucleophiles. The results show that, the electrogenerated phthalazine-1,4-dione (1ox) participates in a Michael type addition reaction with 2a or 2b and via an EC mechanism to produce the corresponding sulfonamide derivatives. This method provides a one-pot procedure for the synthesis of new sulfonamide derivatives of potential biological significance in good yields without using toxic reagents at a carbon electrode in an environmentally friendly manner.
-
-
-
[1]
[1] Z. Huang, Z. Lin, J. Huang, A novel kind of antitumour drugs using sulfonamide as parent compound, Eur. J. Med. Chem. 36 (2001) 863-872.
-
[2]
[2] S.F. Yang, C.F. Lin, C.J. Wu, K.K. Ng, A.Y.C. Lin, P.K.A. Hong, Fate of sulfonamide antibiotics in contact with activated sludge—sorption and biodegradation, Water Res. 46 (2012) 1301-1308.
-
[3]
[3] K. Seri, K. Sanai, K. Kurashima, Y. Imamura, H. Akita, (R)-ACX is a novel sufonylurea compound with potent, quick and short-lasting hypoglycemic activity, Eur. J. Pharmacol. 389 (2000) 253-256.
-
[4]
[4] S. Bano, J. Javed, S. Ahmad, I.G. Rathish, S. Singh, M.S. Alam, Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents, Eur. J. Med. Chem. 46 (2011) 5763-5768.
-
[5]
[5] X.P. Hong, J.Y. Ma, Electrochemical study of sulfadiazine on a novel phthalocyanine- containing chemically modified electrode, Chin. Chem. Lett. 24 (2013) 329- 331.
-
[6]
[6] R. Sivakumar, S.K. Gnanasam, S. Ramachandran, Pharmacological evaluation of some new 1-substituted-4-hydroxy-phthalazines, Eur. J. Med. Chem. 37 (2002) 79-8013.
-
[7]
[7] S.L. Zhang, Y.J. Liu, Y.F. Zhao, Q.T. Guo, P. Gong, Synthesis and antitumor activities of novel 1,4-substituted phthalazine derivatives, Chin. Chem. Lett. 21 (2010) 1071-1074.
-
[8]
[8] X. Zhai, J. Li, L. He, S. Zheng, Y.B. Zhang, P. Gong, Synthesis and in vitro cytotoxicity of novel 1,4-disubstituted phthalazines, Chin. Chem. Lett. 19 (2008) 29-32.
-
[9]
[9] D. Nematollahi, A. Maleki, Electrochemical oxidaton of N,N-dialkyl-π-πhenylenediaminesin the presence of arylsulfinic acids. An efficient method for the synthesisof new sulfonamide derivatives, Electrochem. Commun. 11 (2009) 488-491.
-
[10]
[10] D. Nematollahi, E. Mehdipour, A. Zeinodini-Meimand, A. Maleki, Chemical and electrochemical oxidative coupling of N,N-dialkyl-π-πhenylenediamines and arylsulfinic acids. Synthesis of sulfonamide derivatives, Tetrahedron Lett. 51 (2010) 6447-6450.
-
[11]
[11] F. Varmaghani, D. Nematollahi, S.E. Mallakpour, R. Esmaili, Electrochemical oxidation of 4-substituted urazoles in the presence of arylsulfinic acids: an efficient method for the synthesis of new sulfonamide derivatives, Green Chem. 14 (2012) 963-967.
-
[12]
[12] F. Varmaghani, D. Nematollahi, Electrochemical study of 1,2-dihydropyridazine- 3,6-dione in protic and aprotic solvents: oxidative ring cleavage and reduction, Electrochim. Acta 56 (2011) 6089-6160.
-
[1]
-
-
-
[1]
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
-
[2]
Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
-
[3]
Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
-
[4]
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
-
[5]
Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
-
[6]
Xubin Qian , Lei Xu , Xu Ge , Zhun Liu , Cheng Fang , Jianbing Wang , Junfeng Niu . Can perfluorooctanoic acid be effectively degraded using β-PbO2 reactive electrochemical membrane?. Chinese Chemical Letters, 2024, 35(7): 109218-. doi: 10.1016/j.cclet.2023.109218
-
[7]
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
-
[8]
Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
-
[9]
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
-
[10]
Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
-
[11]
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
-
[12]
Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co6}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
-
[13]
Hong-Rui Li , Xia Kang , Rui Gao , Miao-Miao Shi , Bo Bi , Ze-Yu Chen , Jun-Min Yan . Interfacial interactions of Cu/MnOOH enhance ammonia synthesis from electrochemical nitrate reduction. Chinese Chemical Letters, 2025, 36(2): 109958-. doi: 10.1016/j.cclet.2024.109958
-
[14]
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
-
[15]
Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
-
[16]
Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
-
[17]
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
-
[18]
Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
-
[19]
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
-
[20]
Muhammad Humayun , Mohamed Bououdina , Abbas Khan , Sajjad Ali , Chundong Wang . Designing single atom catalysts for exceptional electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100193-100193. doi: 10.1016/j.cjsc.2023.100193
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(696)
- HTML views(15)