Citation: Liu Jiaxin, Huang Danfeng, Wang Xiaoping, Zong Wuzhong, Su Yingpeng, Wang Kehu, Hu Yulai. Tin Powder Promoted Synthesis of α-Trifluoromethyl Homoallylic Hydrazides[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1767-1775. doi: 10.6023/cjoc201901007 shu

Tin Powder Promoted Synthesis of α-Trifluoromethyl Homoallylic Hydrazides

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Huang Danfeng, huangdf@nwnu.edu.cn
Received Date: 7 January 2019
Revised Date: 29 January 2019
Available Online: 22 June 2019
Fund Project: the National Natural Science Foundation of China 21462037Project supported by the National Natural Science Foundation of China (Nos. 21861033, 21462037)the National Natural Science Foundation of China 21861033

Figures(3)

An efficient multicomponent one-pot reaction was developed for the synthesis of α-trifluoromethyl homoallylic hydrazides from the reactions of ethyl trifluoropyruvate, hydrazides and allylic bromide with tin powder in the presence of Brønsted and Lewis acid in 1, 4-dioxane under reflux. The method avoids the use of toxic stannanes and allows easy operation. The reaction proceeds smoothly under mild reaction conditions to give the corresponding products in good yields.
- one-pot,
- tin powder,
- ethyl trifluoropyruvate,
- α-trifluoromethyl homoallylic hydrazides
1. [1]
  (a) Ke, S.; Sun, T.; Liang, Y.; Yang, Z. Chin. J. Org. Chem. 2010, 30, 1820 (in Chinese).
  (柯少勇, 孙婷婷, 梁英, 杨自文, 有机化学, 2010, 30, 1820.)
  (b) Cui, Z.-N.; Wang, Z.; Li, Y.; Zhou, X.-Y.; Ling, Y.; Yang, X.-L. Chin. J. Org. Chem. 2007, 27, 1300 (in Chinese).
  (崔紫宁, 王振, 李映, 周心玉, 凌云, 杨新玲, 有机化学, 2007, 27, 1300.)
  (c) Aubin, S.; Martin, B.; Delcros, J.-G.; Arlot-Bonnemains, Y.; Baudy-Floc'h, M. J. Med. Chem. 2005, 48, 330.
  (d) Huang, R.; Wang, Q. J. Organomet. Chem. 2001, 637, 94.
2. [2]
  (a) Wing, K. D. Science 1988, 241, 467.
  (b) Wing, K. D.; Slawecki, R. A.; Carlson, G. R. Science 1988, 241, 470.
3. [3]
  (a) Vardanyan, R.; Hruby, V. Synthesis of Essential Drugs, 1st ed., Elsevier Science, Maryland Heights, 2006, pp. 110~112.
  (b) Mashkovskiy, M. D. Khim.-Farm. Zh. 1976, 10, 3.
4. [4]
  (a) Heinzelman, R. V.; Szmuszkovicz, J. Prog. Drug Res. 1963, 6, 85.
  (b) Nogrady, T.; Morris, L. J. Med. Chem. 1966, 9, 438.
5. [5]
  (a) Grande, F.; Aiello, F.; De Grazia, O.; Brizzi, A.; Garofalo, A.; Neamati, N. Bioorg. Med. Chem. 2007, 15, 288.
  (b) Zheng, L.-W.; Wu, L.-L.; Zhao, B.-X.; Dong, W.-L.; Miao, J.-Y. Bioorg. Med. Chem. 2009, 17, 1957.
  (c) Lian, S.; Su, H.; Zhao, B.-X.; Liu, W.-Y.; Zheng, L.-W.; Miao, J.-Y. Bioorg. Med. Chem. 2009, 17, 7085.
6. [6]
  (a) Todeschini, A. R.; de Miranda, A. L. P.; da Silva, K. C. M.; Parrini, S. C.; Barreiro, E. J. Eur. J. Med. Chem. 1998, 33, 189.
  (b) Duarte, C. D.; Tributino, J. L. M.; Lacerda, D. I.; Martins, M. V.; Alexandre-Moreira, M. S.; Dutra, F.; Bechara, E. J. H.; De-Paula, F. S.; Goulart, M. O. F.; Ferreira, J.; Calixto, J. B.; Nunes, M. P.; Bertho, A. L.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. Bioorg. Med. Chem. 2007, 15, 2421.
7. [7]
  (a) Thompson, S. K.; Halbert, S. M.; DesJarlais, R. L.; Tomaszek, T. A.; Levy, M. A.; Tew, D. G.; Ijames, C. F.; Veber, D. F. Bioorg. Med. Chem. 1999, 7, 599.
  (b) Khan, K. M.; Shujaat, S.; Rahat, S.; Hayat, S.; Atta-ur-Rahman; Choudhary, M. I. Chem. Pharm. Bull. 2002, 50, 1443.
  (c) Ersmark, K.; Nervall, M.; Hamelink, E.; Janka, L. K.; Clemente, J. C.; Dunn, B. M.; Blackman, M. J.; Samuelsson, B.; Å qvist, J.; Hallberg, A. J. Med. Chem. 2005, 48, 6090.
8. [8]
  (a) Cui, H.; Xu, Y.; Zhang, Z.-F. Anal. Chem. 2004, 76, 4002.
  (b) Kanie, K.; Yasuda, T.; Ujiie, S.; Kato, T. Chem. Commun. 2000, 1899.
  (c) Parra, M.; Hidalgo, P.; Barberá, J.; Carrasco, E.; Saavedra, C. Liq. Cryst. 2006, 33, 391.
  (d) Yoneya, M.; Takada, S.; Maeda, Y.; Yokoyama, H. Liq. Cryst. 2008, 35, 339.
9. [9]
  (a) Licandro, E.; Perdicchia, D. Eur. J. Org. Chem. 2004, 2004, 665.
  (b) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev. 2014, 114, 2942.
  (c) Flagstad, T.; Petersen, M. T.; Nielsen, T. E. Angew. Chem., Int. Ed. 2015, 54, 8395.
  (d) Zhang, W.; Sun, J.; Xu, F.; Zhu, H.; Yue, R.; Zhang, Y.; Niu, F. Chin. J. Org. Chem. 2017, 37, 3191 (in Chinese).
  (张文婷, 孙健, 徐飞, 朱红, 岳瑞雪, 张毅, 钮福祥, 有机化学, 2017, 37, 3191.)
  (e) Wang, Y.; Wang, K.-H.; Su, Y.; Yang, Z.; Wen, L.; Liu, L.; Wang, J.; Huang, D.; Hu, Y. J. Org. Chem. 2018, 83, 939.
  (f) Yan, Y.; Zhang, Z.; Wan, Y.; Zhang, G.; Ma, N.; Liu, Q. J. Org. Chem. 2017, 82, 7957.
  (g) Flood, D. T.; Hintzen, J. C. J.; Bird, M. J.; Cistrone, P. A.; Chen, J. S.; Dawson, P. E. Angew. Chem., Int. Ed. 2018, 57, 11634.
10. [10]
  (a) Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66 (in Chinese).
  (苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.)
  (b) Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060 (in Chinese).
  (惠人杰, 张士伟, 谭政, 吴小培, 冯柏年, 有机化学, 2017, 37, 3060.)
  (c) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
  (d) Kirk, K. L. Curr. Top. Med. Chem. 2006, 6, 1447.
  (e) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
  (f) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
  (g) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
  (h) Cametti, M.; Crousse, B.; Metrangolo, P.; Milani, R.; Resnati, G. Chem. Soc. Rev. 2012, 41, 31.
11. [11]
  (a) Formicola, L.; Maréchal, X.; Basse, N.; Bouvier-Durand, M.; Bonnet-Delpon, D.; Milcent, T.; Reboud-Ravaux, M.; Ongeri, S. Bioorg. Med. Chem. Lett. 2009, 19, 83.
  (b) Onnis, V.; Cocco, M. T.; Fadda, R.; Congiu, C. Bioorg. Med. Chem. 2009, 17, 6158.
12. [12]
  (a) Xu, Y.; Huang, D.; Wang, K.-H.; Ma, J.; Su, Y.; Fu, Y.; Hu, Y. J. Org. Chem. 2015, 80, 12224.
  (b) Wang, J.; Huang, D.; Wang, K.-H.; Peng, X.; Su, Y.; Hu, Y.; Fu, Y. Org. Biomol. Chem. 2016, 14, 9533.
  (c) Wang, K.-H.; Wang, J.; Wang, Y.; Su, Y.; Huang, D.; Fu, Y.; Du, Z.; Hu, Y. Synthesis 2018, 50.
13. [13]
  Chen, W. J.; Liao, D. H. Chem. World 2006, (5), 285 (in Chinese). doi: 10.3969/j.issn.0367-6358.2006.05.010
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
5. [5]
  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
6. [6]
  Xingxing Jiang , Yuxin Zhao , Yan Kong , Jianju Sun , Shangzhao Feng , Xin Lu , Qi Hu , Hengpan Yang , Chuanxin He . Support effect and confinement effect of porous carbon loaded tin dioxide nanoparticles in high-performance CO₂ electroreduction towards formate. Chinese Chemical Letters, 2025, 36(1): 109555-. doi: 10.1016/j.cclet.2024.109555
7. [7]
  Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
8. [8]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118
9. [9]
  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
10. [10]
  Han Yuan , Fengcai Zhang , Hongzhe Huang , Jiafei Wu , Yi Yang , Wanyi Huang , Dongjing Yang , Zhuoming Li , Zhe Li , Ling Huang , Yi-You Huang , Hai-Bin Luo , Lei Guo . Discovery of 3-trifluoromethyl-substituted pyrazoles as selective phosphodiesterase 10A inhibitors for orally attenuating isoprenaline-induced cardiac hypertrophy. Chinese Chemical Letters, 2025, 36(4): 109965-. doi: 10.1016/j.cclet.2024.109965
11. [11]
  Shicheng Dong , Jun Zhu . Could π-aromaticity cross an unsaturated system to a fully saturated one?. Chinese Chemical Letters, 2024, 35(6): 109214-. doi: 10.1016/j.cclet.2023.109214
12. [12]
  Yan Chen , Xinnan Wang , Yifan Lin , Chun Liu . Shape/dimension-controllable organic heterostructures from one monomer pair. Chinese Chemical Letters, 2025, 36(3): 109903-. doi: 10.1016/j.cclet.2024.109903
13. [13]
  Qingyan JIANG , Yanyong SHA , Chen CHEN , Xiaojuan CHEN , Wenlong LIU , Hao HUANG , Hongjiang LIU , Qi LIU . Constructing a one-dimensional Cu-coordination polymer-based cathode material for Li-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 657-668. doi: 10.11862/CJIC.20240004
14. [14]
  Deqi Fan , Yicheng Tang , Yemei Liao , Yan Mi , Yi Lu , Xiaofei Yang . Two birds with one stone: Functionalized wood composites for efficient photocatalytic hydrogen production and solar water evaporation. Chinese Chemical Letters, 2024, 35(9): 109441-. doi: 10.1016/j.cclet.2023.109441
15. [15]
  Changle Liu , Mingyuzhi Sun , Haoran Zhang , Xiqian Cao , Yuqing Li , Yingtang Zhou . All in one doubly pillared MXene membrane for excellent oil/water separation, pollutant removal, and anti-fouling performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100355-100355. doi: 10.1016/j.cjsc.2024.100355
16. [16]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
17. [17]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
18. [18]
  Fengshun Wang , Huachao Ji , Zefei Wu , Kang Chen , Wenqi Gao , Chen Wang , Longlu Wang , Jianmei Chen , Dafeng Yan . The advanced development of one-dimensional transition metal dichalcogenide nanotubes: From preparation to application. Chinese Chemical Letters, 2025, 36(5): 109898-. doi: 10.1016/j.cclet.2024.109898
19. [19]
  Linlin Yu , Xueli Liu , Rui Gao , Jialin Ming , Yi Qiu , Jie Su , Liangbing Gan . Selective preparation of 18-membered open-cage fullerene with one imino and five carbonyl groups on the rim of the orifice. Chinese Chemical Letters, 2025, 36(6): 110382-. doi: 10.1016/j.cclet.2024.110382
20. [20]
  Tao Ban , Xi-Yang Yu , Hai-Kuo Tian , Zheng-Qing Huang , Chun-Ran Chang . One-step conversion of methane and formaldehyde to ethanol over SA-FLP dual-active-site catalysts: A DFT study. Chinese Chemical Letters, 2024, 35(4): 108549-. doi: 10.1016/j.cclet.2023.108549

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(641)
HTML views(37)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142