BmmimOAc-Catalyzed Direct Condensation of 2-(Arylamino) Alcohols to Synthesize 3-Arylthiazolidine-2-thiones
- Corresponding author: GAO Guohua, ghgao@chem.ecnu.edu.cn †Authors contributed equally to this work
Citation:
CHEN Bihua, ELAGEED Elnazeer H. M., ZHANG Yongya, GAO Guohua. BmmimOAc-Catalyzed Direct Condensation of 2-(Arylamino) Alcohols to Synthesize 3-Arylthiazolidine-2-thiones[J]. Acta Physico-Chimica Sinica,
;2018, 34(8): 952-958.
doi:
10.3866/PKU.WHXB201803081
Prabhakar Y. S., Solomon V. R., Gupta M. K., Katti S. B.. QSAR Studies on Thiazolidines: A Biologically Privileged Scaffold[J]. In QSAR and Molecular Modeling Studies in Heterocyclic Drugs Ⅱ; Gupta S. P...Ed.; Springer: Berlin, Germany, 2006:pp. 161-249.
Chen, N.; Du, H.; Liu, W.; Wang, S.; Li, X.; Xu, J. Phosphorus Sulfur Silicon 2015, 190, 112. doi: 10.1080/10426507.2014.931399
doi: 10.1080/10426507.2014.931399
Almeida, A. M.; Oliveira, B. A.; Castro, P. P.; Mendon a, C. C.; Furtado, R. A.; Diniz, H. N.; Silva, V. L.; Diniz, C. G.; Tavares, D. C.; Silva, H.; et al. Biometals 2017, 30, 841. doi: 10.1007/s10534-017-0046-6
doi: 10.1007/s10534-017-0046-6
Li, R.; Ning, X.; Zhou, S.; Lin, Z.; Wu, X.; Chen, H.; Bai, X.; Wang, X.; Ge, Z.; Li, R.; et al. Eur. J. Med. Chem. 2018, 143, 48. doi: 10.1016/j.ejmech.2017.11.023
doi: 10.1016/j.ejmech.2017.11.023
Corrêa, R. S.; Silva, M. M.; Graminha, A. E.; Meira, C. S.; Santos, J. A. F.; Moreira, D. R. M.; Soares, M. B. P.; Poelhsitz, G. V.; Castellano, E. E.; Bloch, C.; et al. J. Inorg. Biochem. 2016, 156, 153. doi: 10.1016/j.jinorgbio.2015.12.024
doi: 10.1016/j.jinorgbio.2015.12.024
Makiabadi, B. J. Sulfur Chem. 2015, 36, 494. doi: 10.1080/17415993.2015.1062097
doi: 10.1080/17415993.2015.1062097
Hirata, T.; Kogiso, H.; Morimoto, K.; Miyamoto, S.; Taue, H.; Sano, S.; Muguruma, N.; Ito, S.; Nagao, Y. Bioorg. Med. Chem. 1998, 6, 2179. doi: 10.1016/S0968-0896(98)00156-4
doi: 10.1016/S0968-0896(98)00156-4
Yamada, S. Tetrahedron Lett. 1992, 33, 2171. doi: 10.1016/0040-4039(92)88169-6
doi: 10.1016/0040-4039(92)88169-6
Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391. doi: 10.1021/jo00362a047
doi: 10.1021/jo00362a047
Lobana, T. S.; Rani, A.; Butt, Y. N.; Jasinski, J. P. J. Sulfur Chem. 2015, 36, 251. doi: 10.1080/17415993.2015.1023802
doi: 10.1080/17415993.2015.1023802
Fabretti, A. C.; Ferrari, M.; Franchini, G. C.; Preti, C.; Tassi, L.; Tosi, G. Transit. Met. Chem. 1982, 7, 279. doi: 10.1007/BF00618715
doi: 10.1007/BF00618715
Clapp, L. B.; Watjen, J. W. J. Am. Chem. Soc. 1953, 75, 1490. doi: 10.1021/ja01102a516
doi: 10.1021/ja01102a516
Sudo, A.; Morioka, Y.; Koizumi, E.; Sanda, F.; Endo, T. Tetrahedron Lett. 2003, 44, 7889. doi: 10.1016/j.tetlet.2003.09.011
doi: 10.1016/j.tetlet.2003.09.011
Ziyaei-Halimehjani, A.; Marjani, K.; Ashouri, A. Tetrahedron Lett. 2012, 53, 3490. doi: 10.1016/j.tetlet.2012.04.129
doi: 10.1016/j.tetlet.2012.04.129
Shi, M.; Shen, Y. Heteroatom Chem. 2001, 12, 610. doi: 10.1002/hc.1092
doi: 10.1002/hc.1092
Shen, Y.; Shi, M. Appl. Organometal. Chem. 2003, 17, 767. doi: 10.1002/aoc.497
doi: 10.1002/aoc.497
Taguchi, T.; Kiyoshima, Y.; Komori, O.; Mori, M. Tetrahedron Lett. 1969, 10, 3631. doi: 10.1016/S0040-4039(01)88473-2
doi: 10.1016/S0040-4039(01)88473-2
Delaunay, D; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604. doi: 10.1021/jo00125a059
doi: 10.1021/jo00125a059
Chen, N.; Jia, W.; Xu, J. X. Eur. J. Org. Chem. 2009, 5841. doi: 10.1002/ejoc.200900759
doi: 10.1002/ejoc.200900759
Welton, T. Chem. Rev. 1999, 99, 2071. doi: 10.1021/cr980032t
doi: 10.1021/cr980032t
Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508. doi: 10.1021/cr1003248
doi: 10.1021/cr1003248
Zhang, P.; Wu, T.; Han, B. Adv. Mater. 2014, 26, 6810. doi: 10.1002/adma.201305448
doi: 10.1002/adma.201305448
Zhang, Z.; Song, J.; Han, B. Chem. Rev. 2017, 117, 6834. doi: 10.1021/acs.chemrev.6b00457
doi: 10.1021/acs.chemrev.6b00457
MacFarlane, D. R.; Pringle, J. M.; Johansson, K. M.; Forsyth, S. A.; Forsyth, M. Chem. Commun. 2006, 1905. doi: 10.1039/B516961P
doi: 10.1039/B516961P
Zhang, L.; Fu, X.; Gao, G. ChemCatChem 2011, 3, 1359. doi: 10.1002/cctc.201100016
doi: 10.1002/cctc.201100016
Wang, B.; Elageed, E. H. M.; Zhang, D.; Yang, S.; Wu, S.; Zhang, G.; Gao, G. ChemCatChem 2014, 6, 278. doi: 10.1002/cctc.201300801
doi: 10.1002/cctc.201300801
Wang, B.; Yang, S.; Min, L.; Gu, Y.; Zhang, Y.; Wu, X.; Zhang, L.; Elageed, E. H. M.; Wu, S.; Gao, G. Adv. Synth. Catal. 2014, 356, 3125. doi: 10.1002/adsc.201400026
doi: 10.1002/adsc.201400026
Elageed, E. H. M.; Wang, B.; Zhang, Y.; Wu, S.; Gao, G. J. Mol. Catal. A: Chem. 2015, 408, 271. doi: 10.1016/j.molcata.2015.07.034
doi: 10.1016/j.molcata.2015.07.034
Zhang, L.; Yang, S.; Gao, G. Chin. J. Catal. 2011, 32, 1875. doi: 10.3724/SP.J.1088.2011.10757
doi: 10.3724/SP.J.1088.2011.10757
Elageed, E. H. M.; Chen, B.; Wang, B.; Zhang, Y.; Wu, S.; Liu, X.; Gao, G. Eur. J. Org. Chem. 2016, 3650. doi: 10.1002/ejoc.201600474
doi: 10.1002/ejoc.201600474
Zhang, Y.; Wang, B.; Elageed, E. H. M.; Qin, L.; Ni, B.; Liu, X.; Gao, G. ACS Macro. Lett. 2016, 5, 435. doi: 10.1021/acsmacrolett.6b00178
doi: 10.1021/acsmacrolett.6b00178
Zhang, Y.; Zhang, Y.; Chen, B.; Qin, L.; Gao, G. ChemistrySelect2017, 2, 9443. doi: 10.1002/slct.201702081
doi: 10.1002/slct.201702081
Caba o, M. I.; Besnard, M.; Chavez, F. V.; Pinaud, N.; Sebastiao, P. J.; Coutinho, J. A. P.; Mascetti, J.; Danten, Y. Chem. Commun. 2013, 49, 11083. doi: 10.1039/c3cc46038j
doi: 10.1039/c3cc46038j
Caba o, M. I.; Besnard, M.; Chavez, F. V.; Pinaud, N.; Sebastiao, P. J.; Coutinho, J. A. P.; Danten, Y. J. Chem. Phys. 2014, 140, 244307. doi: 10.1063/1.4884820
doi: 10.1063/1.4884820
Wang, B.; Qin, L.; Mu, T.; Xue, Z.; Gao, G. Chem. Rev. 2017, 117, 7113. doi: 10.1021/acs.chemrev.6b00594
doi: 10.1021/acs.chemrev.6b00594
Chen, X.; Song, H.; Chen, P.; Wang, F.; Qian, Y.; Li, X. Acta Chim. Sin. 2012, 70, 770.
doi: 10.6023/A1108223
Ortiz, A.; Sansinenea, E. J. Sulfur Chem. 2007, 28, 109. doi: 10.1080/17415990601139699
doi: 10.1080/17415990601139699
Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
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
Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO2 reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
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
Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
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
Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
Rui Wang , Yuan Tian , Xuefeng Gao , Lei Jiang . Design and fabrication of triangle-pattern superwettability hybrid surface with high-efficiency condensation heat transfer performance. Chinese Chemical Letters, 2025, 36(3): 110395-. doi: 10.1016/j.cclet.2024.110395
Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H2O2 production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526