研究论文

三氟甲基酰腙N-烃基化反应研究

  • 杨金宇 ,
  • 黄丹凤 ,
  • 王克虎 ,
  • 王君姣 ,
  • 苏瀛鹏 ,
  • 邓周斌 ,
  • 杨天宇 ,
  • 胡雨来
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  • 1 西北师范大学化学化工学院 兰州 730070

收稿日期: 2020-11-02

  修回日期: 2020-12-24

  网络出版日期: 2021-02-07

基金资助

国家自然科学基金(21662030); 国家自然科学基金(22061037)

Study on N-Alkylation Reactions of Trifluoromethylated Acylhydrazones

  • Jinyu Yang ,
  • Danfeng Huang ,
  • Kehu Wang ,
  • Junjiao Wang ,
  • Yingpeng Su ,
  • Zhoubin Deng ,
  • Tianyu Yang ,
  • Yulai Hu
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  • 1 College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
* Corresponding author. E-mail:

Received date: 2020-11-02

  Revised date: 2020-12-24

  Online published: 2021-02-07

Supported by

National Natural Science Foundation of China(21662030); National Natural Science Foundation of China(22061037)

摘要

探索了三氟甲基酰腙的N-烃基化反应, 得到了一系列N-烃基取代的三氟甲基酰腙衍生物. 其结构经1H NMR和13C NMR、HRMS等确证. 该方法具有反应条件温和、产率高及操作简单等优点, 为合成N-烃基取代的三氟甲基酰腙类化合物提供了一种简单高效的方法.

本文引用格式

杨金宇 , 黄丹凤 , 王克虎 , 王君姣 , 苏瀛鹏 , 邓周斌 , 杨天宇 , 胡雨来 . 三氟甲基酰腙N-烃基化反应研究[J]. 有机化学, 2021 , 41(5) : 2029 -2037 . DOI: 10.6023/cjoc202011001

Abstract

The N-alkylation reaction of trifluoromethylated acylhydrazones was investigated, and a series of N-alkyl trifluoromethyl acylhydrazones were afforded in good yield. Their structures were confirmed by 1H NMR, 13C NMR and HRMS analysis. The strategy has advantages of simple and mild reaction conditions, wide scope of substrates and good yields. This protocol provides an efficient and new method for the synthesis of N-alkyl substituted trifluoromethyl acylhydrazones.

参考文献

[1]
Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2005, 44, 5176.
[2]
(a) Che, Z.; Zhang, S.; Shao, Y.; Fan, L.; Xu, H.; Yu, X.; Zhi, X.; Yao, X. J. Agric. Food Chem. 2013, 61, 5696.
[2]
(b) Zhou, Y.; Luo, Y.; Yang, Y.-S.; Lu, L.; Zhu, H.-L. Med. Chem. Commun. 2016, 7, 1980.
[2]
(c) Roth, H. S.; Hergenrother, P. J. Curr. Med. Chem. 2016, 23, 201.
[2]
(e) Dimmock, J. R.; Vashishtha, S. C.; Stables, J. P. Eur. J. Med. Chem. 2000, 35, 241.
[3]
Silva, A. G.; Zapata-Sudo, G.; Kummerle, A. E.; Fraga, C. A.; Barreiro, E. J.; Sudo, R. T. Bioorg. Med. Chem. 2005, 13, 3431.
[4]
de Figueiredo, L. P.; Ibiapino A.L. do Amaral D. N.; Ferraz, L. S.; Rodrigues T.; Barreiro E. J.; Lima, L. M.; Ferreira F. F. J. Mol. Struct. 2017, 1147, 226.
[5]
Ku?mmerle, A. E.; Schmitt, M.; Cardozo, S. V. S.; Lugnier, C.; Villa, P.; Lopes, A. B.; Romeiro, N. C.; Justiniano, H.; Martins, M. A.; Fraga, C. A. M.; Bourguignon, J.-J.; Barreiro, E. J. J. Med. Chem. 2012, 55, 7525.
[6]
Rodrigues, D. A.; Ferreira-Silva, G. A.; Ferreira, A. C. S.; Fernandes, R. A.; Kwee, J. K.; Sant'Anna, C. M. R.; Ionta, M.; Fraga, C. A. J. Med. Chem. 2016, 59, 655.
[7]
Vantomme, G.; Jiang, S.; Lehn, J.-M. J. Am. Chem. Soc. 2014, 136, 9509.
[8]
(a) Shih, M.-H.; Xu, Y.-Y.; Yang, Y.-S.; Lin, T.-T. Molecules 2015, 20, 5184.
[8]
(b) Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205.
[9]
Kümmerle, A. E.; Raimundo, J. M.; Leal, C. M.; da Silva, G. S.; Balliano, T. L.; Pereira, M. A.; de Simone, C. A.; Sudo, R. T.; Zapata-Sudo, G.; Fraga, C. A. M.; Barreiro, E. J. Eur. J. Med. Chem. 2009, 44, 4004.
[10]
Oikawa, N.; Müller, C.; Kunz, M.; Lichtenthaler, F. W. Carbohydr. Res. 1998, 309, 269.
[11]
Zhang, H.; Wang, K.-H.; Wang, J.; Su, Y.; Huang, D.; Hu, Y. Org. Biomol. Chem. 2019, 17, 2940.
[12]
Mahmoud, N. F. H.; Elsayed, G. A. J. Heterocycl. Chem. 2020, 57, 1845.
[13]
(a) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Acen?a, J. L.; Soloshonok, V. A.; Lzawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[13]
(b) Vitale, A.; Bongiovanni, R.; Ameduri, B. Chem. Rev. 2015, 115, 8835.
[14]
(a) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
[14]
(b) Charpentier, J.; Fru?h, N.; Togni, A. Chem. Rev. 2015, 115, 650.
[14]
(c) Studer, A. Angew. Chem.,Int. Ed. 2012, 51, 8950.
[15]
(a) Ji, X.; Shi, G.; Zhang, Y. Chin. J. Org. Chem. 2019, 39, 929. (in Chinese).
[15]
(季小明, 史广法, 张扬会, 有机化学, 2019, 39, 929.)
[15]
(b) Qing, F. Chin. J. Org. Chem. 2012, 32, 815. (in Chinese).
[15]
(卿凤翎, 有机化学, 2012, 32, 815.)
[15]
(c) Liang, H.; Xu, G.; Feng, Z.; Wang, Z.; Xu, P. J. Org. Chem. 2019, 84, 60.
[15]
(d) Wang, J.; Li, F.; Xu, Y.; Wang, J.; Wu, Z.; Yang, C.; Liu, L. Chin. J. Org. Chem. 2018, 38, 1155. (in Chinese).
[15]
(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.)
[16]
(a) Wang, K.-H.; Shi, B.; Wang, Y.; Wang, J.; Huang, D.; Su, Y.; Hu, Y. Asian J. Org. Chem. 2019, 8, 716.
[16]
(b) Xu, W.; Huang, D.; Wang, K.; Zhao, F.; Zhao, Z.; Hu, Y.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2020, 40, 922. (in Chinese).
[16]
(徐炜刚, 黄丹凤, 王克虎, 赵芳霞, 赵转霞, 虎永琴, 苏瀛鹏, 胡雨来, 有机化学, 2020, 40, 922.)
[16]
(c) Hu, Y.; Huang, D.; Wang, K.; Zhao, F.; Zhao, Z.; Xu, W.; Hu, Y. Chin. J. Org. Chem. 2020, 40, 1689. (in Chinese).
[16]
(虎永琴, 黄丹凤, 王克虎, 赵芳霞, 赵转霞, 徐炜刚, 胡雨来, 有机化学, 2020, 40, 1689.)
[17]
(a) Peng, X.; Huang, D.; Wang, K.-H.; Wang, Y.; Wang, J.; Su, Y.; Hu, Y. Org. Biomol. Chem. 2017, 15, 6214.
[17]
(b) Liu, L.; Huang, D.; Wang, Y.; Wen, L.; Yang, Z.; Su, Y.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1469. (in Chinese).
[17]
(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.)
[17]
(c) Zhao, F.; Wang, K.-H.; Wen, L.; Zhao, Z.; Hu, Y.; Xu, W.; Huang, D.; Su, Y.; Wang, J.; Hu, Y. Asian J. Org. Chem. 2020, 9, 1036.
[18]
Du, G.; Huang, D.; Wang, K. H.; Chen, X.; Xu, Y.; Ma, J.; Su, Y.; Hu, Y. Org. Biomol. Chem. 2016, 14, 1492.
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