研究论文

三氟甲基酰腙的氰基化反应研究

  • 徐炜刚 ,
  • 黄丹凤 ,
  • 王克虎 ,
  • 赵芳霞 ,
  • 赵转霞 ,
  • 虎永琴 ,
  • 苏瀛鹏 ,
  • 胡雨来
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  • 西北师范大学化学化工学院 兰州 730070

收稿日期: 2019-10-11

  修回日期: 2019-12-10

  网络出版日期: 2019-12-27

基金资助

国家自然科学基金(Nos.21662030,21861033)资助项目.

Study on the Hydrocyanation Reaction of Trifluoromethylated Acylhydrazones

  • Xu Weigang ,
  • Huang Danfeng ,
  • Wang Kehu ,
  • Zhao Fangxia ,
  • Zhao Zhuanxia ,
  • Hu Yongqing ,
  • Su Yingpeng ,
  • Hu Yulai
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2019-10-11

  Revised date: 2019-12-10

  Online published: 2019-12-27

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21662030, 21861033).

摘要

探索了在路易斯酸催化下,三氟甲基酰腙与三甲基氰硅烷的1,2-加成反应,得到了一系列含有三氟甲基的氰基酰肼类化合物.该方法具有反应条件温和、操作简单、产率高等特点,为合成结构多样的含三氟甲基的酰肼类化合物提供了一种有效的方法.

本文引用格式

徐炜刚 , 黄丹凤 , 王克虎 , 赵芳霞 , 赵转霞 , 虎永琴 , 苏瀛鹏 , 胡雨来 . 三氟甲基酰腙的氰基化反应研究[J]. 有机化学, 2020 , 40(4) : 922 -929 . DOI: 10.6023/cjoc201910011

Abstract

The Lewis acid catalyzed 1,2-addition reaction of trifluoromethylated acylhydrazones with trimethylsilyl cyanide was investigated, and a series of cyanohydrazide compounds containing trifluoromethyl group were afforded in high yield. The method could be easily operated in mild reaction conditions, which provides an efficient method for the synthesis of trifluoromethylated hydrazides with structural diversity.

参考文献

[1] (a) Chauhan, J.; Ravva, M. K.; Sen, S. Org. Lett. 2019, 21, 6562.
(b) 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.
(c) Tokumaru, K.; Johnston, J. N. Chem. Sci. 2017, 8, 3187.
(d) An, J.; Alper, H.; Beauchemin, A. M. Org. Lett. 2016, 18, 3482.
(e) Fan, Y.; He, Y.; Liu, X.; Hu, T.; Ma, H.; Yang, X.; Luo, X.; Huang, G. J. Org. Chem. 2016, 81, 6820.
(f) Flagstad, T.; Petersen, M. T.; Nielsen, T. E. Angew. Chem., Int. Ed. 2015, 54, 8395.
[2] (a) Yoneya, M.; Takada, S.; Maeda, Y.; Yokoyama, H. Liq. Cryst. 2008, 35, 339.
(b) Parra, M.; Hidalgo, P.; Barberá, J.; Carrasco, E.; Saavedra, C. Liq. Cryst. 2006, 33, 391.
(c) Cui, H.; Xu, Y.; Zhang, Z.-F. Anal. Chem. 2004, 76, 4002.
(d) Zhao, X.; Wang, X.-Z.; Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. J. Am. Chem. Soc. 2003, 125, 15128.
[3] Wing, K. D. Science 1988, 241, 467.
[4] (a) Wheelock, C. E.; Nakagawa, Y.; Harada, T.; Oikawa, N.; Akamatsu, M.; Smagghe, G.; Stefanou, D.; Iatrou, K.; Swevers, L. Bioorg. Med. Chem. 2006, 14, 1143.
(b) Nakagawa, Y. Vitam. Horm. 2005, 73, 131.
(c) Wing, K. D.; Slawecki, R. A.; Carlson, G. R. Science 1988, 241, 470.
[5] (a) Toraskar, M. P.; Kadam, V. J.; Kulkarni, V. M. Int. J. ChemTech Res. 2009, 1, 1194.
(b) Lian, S.; Su, H.; Zhao, B.-X.; Liu, W.-Y.; Zheng, L.-W.; Miao, J.-Y. Bioorg. Med. Chem. 2009, 17, 7085.
(c) 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.
[6] (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.
[7] (a) Schneider, U.; Chen, I.-H; Kobayashi, S. Org. Lett. 2008, 10, 737.
(b) Tan, K. L.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 1315.
(c) Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2005, 44, 5176.
(d) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493.
[8] (a) Alonso, C.; de Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847.
(b) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(c) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
(d) Qing, F. Chin. J. Org. Chem. 2012, 32, 815(in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
(e) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(f) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[9] For selected reviews, see:(a) Moschner, J.; Stulberg, V.; Fernandes, R.; Huhmann, S.; Leppkes, J.; Koksch, B. Chem. Rev. 2019, 119, 10718.
(b) Fustero, S.; Simón-Fuentes, A.; Barrio, P.; Haufe, G. Chem. Rev. 2015, 115, 871.
(c) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
(d) Uneyama, K.; Katagiri, T.; Amii, H. Acc. Chem. Res. 2008, 41, 817.
(e) Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432.
[10] For selected examples, see:(a) Yang, Y.-Y.; Yang, G.; Cheng, C.; Li, Y.-X.; Zhang, J.-Q.; Feng, W.; Zhao, Y.-L.; Tang, L. Org. Lett. 2019, 21, 2236.
(b) Liu, J.; Huang, D.; Wang, X.; Zong, W.; Su, Y.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2019, 39, 1767(in Chinese). (刘佳欣, 黄丹凤, 王小平, 宗吴中, 苏瀛鹏, 王克虎, 胡雨来, 有机化学, 2019, 39, 1767.)
(c) You, Y.; Lu, W.-Y.; Wang, Z.-H.; Chen, Y.-Z.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2018, 20, 4453.
(d) Wang, J.; Li, F.; Xu, Y.; Wang, J.; Wu, Z.; Yang, C.; Liu, L. Chin. J. Org. Chem. 2018, 38, 1155(in Chinese). (王晶晶, 李峰, 徐妍, 王娟, 武紫燕, 杨成玉, 刘澜涛, 有机化学, 2018, 38, 1155.)
(e) Zhang, F.-G.; Lv, N.; Zheng, Y.; Ma, J.-A. Chin. J. Chem. 2018, 36, 723.
[11] (a) Li, J.; Yang, T.; Zhang, H.; Huang, D.; Wang, K.-H.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 925(in Chinese). (李军, 杨天宇, 张怀远, 黄丹凤, 王克虎, 苏瀛鹏, 胡雨来, 有机化学, 2017, 37, 925.)
(b) Li, J.; Huang, D.; Zhang, H.; Zhang, X.; Wang, J.; Wang, K.-H.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 2985(in Chinese). (李军, 黄丹凤, 张怀远, 张兴虎, 王娟娟, 王克虎, 苏瀛鹏, 胡雨来, 有机化学, 2017, 37, 2985.)
(c) Peng, X.; Wang, K.-H.; Huang, D.; Wang, J.; Wang, Y.; Su, Y.; Hu, Y.; Fu, Y. Appl. Organomet. Chem. 2017, 31, 3731.
(d) Du, G.; Huang, D.; Wang, K.-H.; Chen, X.; Xu, Y.; Ma, J.; Su, Y.; Fu, Y.; Hu, Y. Org. Biomol. Chem. 2016, 14, 1492.
[12] (a) Wen, L.; Huang, D.; Wang, K.-H.; Wang, Y.; Liu, L.; Yang, Z.; Su, Y.; Hu, Y. Synthesis 2018, 50, 1979.
(b) Wang, K.-H.; Wang, J.; Wang, Y.; Su, Y.; Huang, D.; Fu, Y.; Du, Z.; Hu, Y. Synthesis 2018, 50, 1907.
(c) Liu, L.; Huang, D.; Wang, Y.; Wen, L.; Yang, Z; Su, Y.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1469(in Chinese). (刘丽丽, 黄丹凤, 王玉祥, 文岚, 杨政, 苏瀛鹏, 王克虎, 胡雨来, 有机化学, 2018, 38, 1469.)
(d) Peng, X.; Huang, D.; Wang, K.-H.; Wang, Y.; Wang, J.; Su, Y.; Hu, Y. Org. Biomol. Chem. 2017, 15, 6214
[13] (a) Zamfir, A.; Tsogoeva, S. B. Org. Lett. 2010, 12, 188.
(b) Keith, J. M.; Jacobsen, E. N. Org. Lett. 2004, 6, 153.
(c) Ding, H.; Friestad, G. K. Heterocycles 2006, 70, 185.
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