Citation:
Pravinkumar N. Sable, Swastika Ganguly, Pravin D. Chaudhari. An effi cient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives[J]. Chinese Chemical Letters,
;2014, 25(7): 1099-1103.
doi:
10.1016/j.cclet.2014.03.044
-
A convenient one-pot three-component method for the preparation of tetra-substituted thiophene derivatives has been developed. Reaction of acetyl acetone 1, phenyl isothiocynate 2 and 2-chloromethyl derivatives 3a-3c in the presence of potassium carbonate afforded the target compounds, namely ethyl 2-(4-acetyl-3-methyl-5-(phenylamino)thiophen-2-yl)-2-oxoacetate derivatives 4a-4e, ethyl 3-(4-acetyl-3-methyl-5-(phenylamino)thiophen-2-yl)-3-oxopropanoate derivatives 4f-4i, di((4-acetyl-3-methyl-5-phenylamino)thiophen-2-yl)ketone derivatives 4j-4n in reasonable overall yields. The synthesized compounds were screened for antimicrobial activity. The detailed synthesis, spectroscopic data and antimicrobial activities of synthesized compounds were reported.
-
-
-
[1]
[1] A. Dömling, W. Wang, K. Wang, Chemistry and biology of multicomponent reactions, Chem. Rev. 112 (2012) 3083-3135.
-
[2]
[2] A. Dömling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.
-
[3]
[3] F.M. Moghaddam, H.Z. Boinee, An efficient and facile one-step synthesis of highly substituted thiophenes, Tetrahedron 60 (2004) 6085-6089.
-
[4]
[4] K.I. Molvi, M. Mansuri, V. Sudarsanam, et al., Synthesis, anti-inflammatory, analgesic and antioxidant activities of some tetrasubstituted thiophenes, J. Enzyme Inhib. Med. Chem. 23 (2008) 829-838.
-
[5]
[5] M.K. Parai, G. Panda, V. Chaturvedi, Y.K. Manju, S. Sinha, Thiophene containing triarylmethanesasantitubercularagents, Bioorg.Med.Chem.Lett.18(2008)289-292.
-
[6]
[6] W. Wardakhan, O. Abdel-Salam, G. Elmegeed, Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives, Acta Pharm. 58 (2008) 1-14.
-
[7]
[7] S. Sharma, F. Athar, M.R. Maurya, A. Azam, Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: synthesis, characterization and antiamoebic activity against E. histolytica, Eur. J. Med. Chem. 40 (2005) 1414-1419.
-
[8]
[8] O.F. William, Principles of Medicinal Chemistry, 3rd ed., Lippincott Williams & Wilkins Publication, Philadelphia, 1989.
-
[9]
[9] A.A. Sagardoy, M.J. Gil, R. Villar, et al., Benzo[b]thiophene-6-carboxamide 1,1-dioxides: inhibitors of human cancer cell growth at nanomolar concentrations, Bioorg. Med. Chem. 18 (2010) 5701-5707.
-
[10]
[10] A.A. Fadda, E. Abdel-Latif, R.E. El-Mekawy, Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives, Eur. J. Med. Chem. 44 (2009) 1250-1256.
-
[11]
[11] Indian Pharmacopoeia, Microbiological Assay of Antibiotics, vol. I, 2007, pp. 45-52.
-
[12]
[12] C.R. Kokare, Pharmaceutical Microbiology and Biotechnology, 3rd ed., Nirali Prakashan, Pune, 2006, pp. 21.1-21.12.
-
[13]
[13] Ananthanarayan, Paniker, Textbook of Microbiology, 7th ed., Orient Longman, Chennai, 2005, pp. 628-630.
-
[14]
[14] Y.J. Huang, A. Dömling, The Gewald multicomponent reaction, Mol. Divers. 15 (2011) 3-33.
-
[1]
-
-
-
[1]
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
-
[2]
Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
-
[3]
Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
-
[4]
Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
-
[5]
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
-
[6]
Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
-
[7]
Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
-
[8]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[9]
Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
-
[10]
Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
-
[11]
Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
-
[12]
Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
-
[13]
Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
-
[14]
Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
-
[15]
Guoliang Gao , Guangzhen Zhao , Guang Zhu , Bowen Sun , Zixu Sun , Shunli Li , Ya-Qian Lan . Recent advancements in noble-metal electrocatalysts for alkaline hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(1): 109557-. doi: 10.1016/j.cclet.2024.109557
-
[16]
Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
-
[17]
Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
-
[18]
Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
-
[19]
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
-
[20]
Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(573)
- HTML views(7)