I2/CuO-Catalyzed One-Pot Synthesis of 3-(2-Amino-4-thiazolyl) Coumarin Derivatives from 3-Acetylcoumarins and Thiourea
- Corresponding author: Hu Shengli, hushengli168@126.com
Citation:
Zhao Fang, Hu Yang, Li Qiao, Hu Shengli. I2/CuO-Catalyzed One-Pot Synthesis of 3-(2-Amino-4-thiazolyl) Coumarin Derivatives from 3-Acetylcoumarins and Thiourea[J]. Chinese Journal of Organic Chemistry,
;2020, 40(4): 1068-1073.
doi:
10.6023/cjoc201908031
Spino, C.; Dodier, M. Sotheeswaran, S. Bioorg. Med. Chem. Lett. 1998, 8, 3475.
doi: 10.1016/S0960-894X(98)00628-3
Witaicenis, A.; Seito, L. N.; Di Stasi, L. C. Chem. Biol. Interact. 2010, 186, 211.
doi: 10.1016/j.cbi.2010.03.045
Arora, R. K.; Kaur, N.; Bansal, Y.; Bansal, G. Acta Pharm. Sin. B 2014, 4, 368.
doi: 10.1016/j.apsb.2014.07.001
Basile, A.; Sorbo, S.; Spadaro, V. Molecules 2009, 14, 939.
doi: 10.3390/molecules14030939
Huang, X.; Liu, J. Chin. J. Org. Chem. 2018, 38, 1233(in Chinese).
Sun, H.; Sun, H.; Liu, M.; Huang, W.; Yang, G. Chin. J. Org. Chem. 2018, 38, 2067(in Chinese).
Fang, Z. X.; Liu, J. Y.; Qiao, Y. H. Chin. J. Org. Chem. 2018, 38, 1985(in Chinese).
Kim, J.; Moon, Y.; Ham, S. W. Bull. Korean Chem. Soc. 2011, 32, 2893.
doi: 10.5012/bkcs.2011.32.8.2893
Ding, C.; Pan, Y.; Yin, X.; Tan, C. Chin. J. Org. Chem. 2019, 39, 2099(in Chinese).
Xu, J.; Ma, L.; Liu, X. B. Chin. J. Org. Chem. 2018, 38, 1680(in Chinese).
Zhang, Q.; Wang, Y.; Zhao, Y.; Ma, C.; Xu, X.; Gu, W.; Yang, Y.; Wang, S. Chin. J. Org. Chem. 2019, 39, 2616(in Chinese).
Koelsch, C. F. J. Am. Chem. Soc. 1950, 72, 2993.
doi: 10.1021/ja01163a053
Vardhan, V. A.; Rao, V. R. Indian J. Chem., Sect. B 1997, 36, 1085.
Ramanna, S.; Rao, V. R.; Kumari, T. S.; Rao, T. V. P. Phosphorus Sulfur Relat. Elem. 1995, 107, 197.
doi: 10.1080/10426509508027935
Czerney, P.; Hartmann, H. J. Prakt. Chem. 1983, 325, 551.
doi: 10.1002/prac.19833250405
Ramagiri, R. K.; Vedula, R. R.; Thupurani, M. K. Phosphorus sulfur Relat. Elem. 2015, 190, 1393.
doi: 10.1080/10426507.2014.990016
Zhuravel, I. O.; Kovalenko, S. M.; Vlasov, S. V.; Chernykh, V. P. Molecules 2005, 10, 444.
doi: 10.3390/10020444
Ramesh, G.; Janardhan, B.; Rajitha, B. Res. Chem. Intermed. 2015, 41, 8099.
doi: 10.1007/s11164-014-1879-z
Chunduru, V. S. R.; Rao, R. V. J. Chem. Res. 2010, 34, 50.
doi: 10.3184/030823410X12627991159610
Saeed, A.; Ejaz, S. A.; Shehzad, M.; Hassan, S.; al-Rashida, M.; Lecka, J.; Sévigny, J.; Iqbal, J. RSC Adv. 2016, 6, 21026.
doi: 10.1039/C5RA24684A
Hande, P. E.; Samui, A. B.; Kulkarni, P. S. Sens. Actuators, B 2017, 246, 597.
doi: 10.1016/j.snb.2017.02.125
Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211.
doi: 10.1039/C1OB06432K
Fan, L.; Yao, C.; Shu, M. Heterocycl. Commun. 2016, 22, 63.
Jadhvar, S. C.; Kasraliker, H. M.; Goswami, S. V.; Chakrawar, A. V.; Bhusare, S. R. Res. Chem. Intermed. 2017, 43, 7211.
doi: 10.1007/s11164-017-3069-2
Jannati, S.; Esmaeili, A. A. Res. Chem. Intermed. 2017, 43, 6817.
doi: 10.1007/s11164-017-3022-4
Reddy, K. M. K.; Sadik, S. M.; Saichaithanya, N.; Peddanna, K.; Reddy, N. B.; Sravya, G.; Grigory V, Z.; Reddy, C. S. Res. Chem. Intermed. 2017, 43, 7087.
doi: 10.1007/s11164-017-3060-y
Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441.
doi: 10.1016/0040-4039(96)00026-3
More, S. V.; Sastry, M. N. V.; Wang, C. C.; Yao, C. F. Tetrahedron Lett. 2005, 46, 6345.
doi: 10.1016/j.tetlet.2005.07.026
Behmadi, H.; Roshani, M.; Saadati, S. M. Chin. Chem. Lett. 2009, 20, 5.
doi: 10.1016/j.cclet.2008.09.047
Zhu, Y. P.; Yuan, J. J.; Zhao, Q.; Lian, M.; Gao, Q. H.; Liu, M. C.; Yang, Y.; Wu, A. X. Tetrahedron 2012, 68, 173.
doi: 10.1016/j.tet.2011.10.074
Bogdal, D. J. Chem. Res., Synop. 1998, 468.
Lin, W.; Cao, X.; Yuan, L. Ding, Y. Chem. Eur. J. 2010, 16, 6454.
doi: 10.1002/chem.201000244
Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I2 interface modification engineering on the performance of all-inorganic CsPbBr3 perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
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
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
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
Zhijie Zhang , Xun Li , Huiling Tang , Junhao Wu , Chunxia Yao , Kui Li . Cs2CuBr4 perovskite quantum dots confined in mesoporous CuO framework as a p-n type S-scheme heterojunction for efficient CO2 photoconversion. Chinese Chemical Letters, 2024, 35(11): 109700-. doi: 10.1016/j.cclet.2024.109700
Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO2 Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe2O3 and NO2 with 2D-COS: The role of SDS, UV and SO2. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
Yu Zhou , Lin-Tao Jiang , Xiao-Ming Jiang , Bin-Wen Liu , Guo-Cong Guo . Mixed-anion square-pyramid [SbS3I2] units causing strong second-harmonic generation intensity and large birefringence. Chinese Chemical Letters, 2025, 36(4): 109740-. doi: 10.1016/j.cclet.2024.109740
Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
Lanfang Wang , Jiangnan Lv , Yujia Li , Yanqing Hao , Wenjiao Liu , Hui Zhang , Xiaohong Xu . One-step synthesis of nanowoven ball-like NiS-WS2 for high-efficiency hydrogen evolution. Chinese Chemical Letters, 2025, 36(1): 109597-. doi: 10.1016/j.cclet.2024.109597
Zheng Zhang , Lei Shi , Bin Wang , Jingyuan Qu , Xiaoling Wang , Tao Wang , Qitao Jiang , Wuhong Xue , Xiaohong Xu . Epitaxial growth of full-vdW α-In2Se3/MoS2 heterostructures for all-in-one sensing and memory-computing artificial visual system. Chinese Chemical Letters, 2025, 36(3): 109687-. doi: 10.1016/j.cclet.2024.109687
Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO2 nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs3Bi2X9 (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO2 adsorption and conversion: Modification methods, reaction condition, and CO2 hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
Lu Dai , Yuxin Ren , Shuang Li , Meidi Wang , Chentao Hu , Ya-Pan Wu , Guangtong Hai , Dong-Sheng Li . Room-temperature synthesis of Co(OH)2/Mo2TiC2Tx hetero-nanosheets with interfacial coupling for enhanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 109774-. doi: 10.1016/j.cclet.2024.109774
Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO2 catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331