Synthesis of 3-Ethanoyl/Aroylacetylindoles in Water
- Corresponding author: Yu Haifeng, yuhf68105@sina.com Wang Wenju, wangwj3309@126.com
Citation:
Hu Xiaoyu, Yu Haifeng, Wang Wenju, Jiang Siao, Liu Qi, He Jie. Synthesis of 3-Ethanoyl/Aroylacetylindoles in Water[J]. Chinese Journal of Organic Chemistry,
;2019, 39(11): 3183-3189.
doi:
10.6023/cjoc201904002
Goldgur, Y.; Craigie, R.; Cohen, G. H.; Fujiwara, T.; Yoshinaga, T.; Fujishita, T.; Sugimoto, H.; Endo, T.; Murai, H.; Davies, D. R. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 13040.
doi: 10.1073/pnas.96.23.13040
Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379.
doi: 10.1016/S0968-0896(02)00239-0
Jain, S. V.; Sonawane, L. V.; Patil, R. R.; Bari, S. B. Med. Chem. Res. 2012, 21, 165.
doi: 10.1007/s00044-010-9520-1
Zhang, D. T.; Wang, G. T.; Tan, C. B.; Xu, W. R.; Pei, Y.; Huo, L. Y. Arch. Pharm. Res. 2011, 34, 343.
doi: 10.1007/s12272-011-0301-2
Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H. H.; Cirrincione, G. Bioorg. Med. Chem. 2010, 18, 4524.
doi: 10.1016/j.bmc.2010.04.061
Carbone, A.; Spanò, V.; Parrino, B.; Ciancimino, C.; Attanasi, O. A.; Favi, G. Molecules 2013, 18, 2518.
doi: 10.3390/molecules18032518
Bergman, J. Acta Chem. Scand. 1968, 22, 1063.
doi: 10.3891/acta.chem.scand.22-1063
Pais, G. C. G.; Zhang, X. C.; Marchand, C.; Neamati, N.; Cowansage, K.; Svarovskaia E. S.; Pathak, V. K.; Tang, Y.; Nicklaus, M.; Pommier, Y.; Burke, T. R. J. Med. Chem. 2002, 45, 3184.
doi: 10.1021/jm020037p
Kostryukova, T. S.; Ivanovskaya, N. P.; Lyamin, A. I.; Romanov, D. V.; Osin, N. S.; Zatonsky, G. V.; Vasil'ev N. V. Russ. J. Gen. Chem. 2012, 82, 455.
doi: 10.1134/S1070363212030152
Yu, H. F.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 956 (in Chinese).
Yu, H. F.; Liao, P. Q.; Diao, Q. P.; Li, T. C.; Xin, G.; Han, L. N.; Hou, D. Y. Chin. J. Org. Chem. 2014, 34, 1851 (in Chinese).
Wang, W. J.; Yu, H. F. Synth. Commun. 2019, 49, 377.
doi: 10.1080/00397911.2018.1555851
Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
doi: 10.1021/ar000145a
Zhou, Z.; Duan, J. F.; Mu, X. J.; Xiao, S. Y. Chin. J. Org. Chem. 2018, 38, 585 (in Chinese).
Xu, Z. H.; Chen, F. B.; Li, Y. Y.; Huang, Q. S.; Liao, C. W. Chin. J. Org. Chem. 2018, 38, 3101 (in Chinese).
Wang, Z.; Yang, L.; Liu, H. L.; Bao, W. H.; Tan, Y. H.; Wang, M.; Tang, Z. L.; He, W. M. Chin. J. Org. Chem. 2018, 38, 2639 (in Chinese).
Xie, L. Y.; Li, Y. J.; Qu, J.; Duan, Y.; Hu, J.; Liu, K. J.; Cao, Z.; He, W. M. Green Chem. 2017, 19, 5642.
doi: 10.1039/C7GC02304A
Xie, L. Y.; Peng, S.; Tan, J. X.; Sun, R. X.; Yu, X. Y.; Dai, N. N.; Tang, Z. L.; Xu, X. H.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 16976.
doi: 10.1021/acssuschemeng.8b04339
Xie, L. Y.; Peng, S.; Liu, F.; Liu, Y. F.; Sun, M.; Tang, Z. L.; Jiang, S.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 77, 7193.
Dong, D. W.; Ouyang, Y.; Yu, H. F.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
doi: 10.1021/jo050271y
Yu, H. F.; Liao, P. Q. Tetrahedron Lett. 2016, 57, 2868.
doi: 10.1016/j.tetlet.2016.05.062
Qi, F.; Yu, H. F.; Wang, Y. N.; Lv, Y.; Li, Y. X.; Han, L.; Wang, R.; Feng, X. N. Synth. Commun. 2017, 47, 2220.
doi: 10.1080/00397911.2017.1368084
Pan, L.; Bi, X. H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.
doi: 10.1039/C2CS35329F
Yu, H. F.; Zhao, L. J.; Diao, Q. P.; Li, T. C.; Liao, P. Q.; Hou, D. Y.; Xin, G. Synlett 2017, 28, 1828.
doi: 10.1055/s-0036-1588982
Zhao H.; Diao, Q. P.; Yu, H. F.; Li, T. C.; Liao, P. Q.; Hou, D. Y. Chem. Res. Chin. Univ. 2017, 33, 746.
doi: 10.1007/s40242-017-7082-1
Yu, H. F.; Jin, W. W.; Sun, C. L.; Yu, Z. K. Angew. Chem., Int. Ed. 2010, 49, 5792.
doi: 10.1002/anie.201002737
Yu, H. F.; Yu, Z. K. Angew. Chem., Int. Ed. 2009, 48, 2929.
doi: 10.1002/anie.200900278
Yu, H. F.; Li, T. C.; Liao, P. Q. Synthesis 2012, 44, 3743.
doi: 10.1055/s-0032-1317691
Wang, Q.; Sun, Y. X.; Cui, S. Y.; Zhao, H.; Huang, W.; Xie, X. H. J. Mianyang Teachers' College 2017, 36, 30 (in Chinese).
Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271
Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
Xinxin Wu . 基础有机化学教学中自由基重排反应的课程设计及其课程思政元素的融入. University Chemistry, 2025, 40(6): 316-325. doi: 10.12461/PKU.DXHX202408055
Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
Zhaoxuan ZHU , Lixin WANG , Xiaoning TANG , Long LI , Yan SHI , Jiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368
Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117