SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 156 - 161

DOI: https://doi.org/10.6023/cjoc201905040

Synthesis of 2,4-Disubstituted Quinolines in Deep Eutectic Solvents

  • Chen Guoqing ,
  • Xie Zongbo ,
  • Liu Yishuai ,
  • Meng Jia ,
  • Le Zhanggao
Expand
  • a State Key Laboratory of Nuclear Resources and Environment, East China University of Technology, Nanchang 330013;
    b Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Received date: 2019-05-19

  Revised date: 2019-07-20

  Online published: 2019-09-05

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21462001, 11765002), and the Science and Technology Projects of Jiangxi Province (Nos. 20161BCB24006, 20181BAB203019).

Fold

Abstract

In the deep eutectic solvent which composed of choline chloride and zinc chloride, a series of 2,4-disubstituted quinolines were synthesized via cyclization coupling of 2-aminoacetophenone and aromatic alkyne. When the molar ratio of choline chloride and zinc chloride was 1:2, the yield up to 98% was achieved at 80℃ for 3 h. The method does not need additional catalyst, and has the advantages of mild reaction conditions, simple operation and a wide range of substrates.

Key words： deep eutectic solvent; choline chloride; zinc chloride; cyclization coupling; 2,4-disubstituted quinoline

Cite this article

Chen Guoqing , Xie Zongbo , Liu Yishuai , Meng Jia , Le Zhanggao . Synthesis of 2,4-Disubstituted Quinolines in Deep Eutectic Solvents[J]. Chinese Journal of Organic Chemistry, 2020 , 40(1) : 156 -161 . DOI: 10.6023/cjoc201905040

References

[1] Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315.
[2] Vaitilingam, B.; Nayyar, A.; Palde, P. B.; Monga, V.; Jain, R.; Kaur, S.; Singh, P. P. Bioorg. Med. Chem. 2004, 12, 4179.
[3] Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668.
[4] Kouznetsov, V. V.; Mendez, L. Y. V.; Gomez, C. M. M. Curr. Org. Chem. 2005, 9, 141.
[5] Ghassamipour, S.; Sardarian, A. R. Tetrahedron Lett. 2009, 50, 514.
[6] Sloop, J. C. J. Phys. Org. Chem. 2009, 22, 110.
[7] Yadav, J. S.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R. Tetrahedron Lett. 2005, 46, 7249.
[8] Shvekhgeimer, M. G. A. Chem. Heterocycl. Com. 2004, 40, 257.
[9] Wang, M. X.; Liu, Y.; Huang, Z. T. Tetrahedron Lett. 2001, 42, 2553.
[10] Zhan, X. Ph.D. Dissertation, Hunan University, Changsha, 2018 (in Chinese). (湛西, 博士论文, 湖南大学, 长沙, 2018.)
[11] Wang, Y.; Peng, C. L.; Liu, L. Y.; Zhao, J. J.; Su, L.; Zhu, Q. Tetrahedron Lett. 2009, 50, 2261.
[12] Cho, H. J.; Török, F.; Török, B. Green Chem. 2014, 16, 3623.
[13] Huang, Y. H.; Wang, S. R.; Wu, D. P.; Huang, P. Q. Org. Lett. 2019, 21, 1681.
[14] Zheng, W. P.; Yang, W. G.; Luo, D. P.; Min, L.; Wang, X. Y.; Hu, Y. F. Adv. Synth. Catal. 2019, 361, 1995.
[15] Li, L. H.; Niu, Z. J.; Liang, Y. M. Chem.-Eur. J. 2017, 23, 15300.
[16] Ye, J. L.; Zhu, Y. N.; Geng, H.; Huang, P. Q. Sci. China:Chem. 2018, 61, 687.
[17] Lu, Y.; Liang, M.; Jiang, G. F.; Xie, Z. B.; Le, Z. G. Fine Chem. 2018, 35, 1427(in Chinese). (卢粤, 梁萌, 姜国芳, 谢宗波, 乐长高, 精细化工, 2018, 35, 1427.)
[18] Liu, P.; Hao, J. W.; Mo, L. P.; Zhang, Z. H. RSC Adv. 2015, 5, 48675.
[19] Zhang, Q. H.; Vigier, K. D. O.; Royer, S.; Jerome, F. Chem. Soc. Rev. 2012, 41, 7108.
[20] Yadav, U. N.; Shankarling, G. S. J. Mol. Liq. 2014, 195, 188.
[21] Chen, Z. Z.; Zhu, W.; Zheng, Z. B.; Zou, X. Z. J. Fluorine Chem. 2010, 131, 340.
[22] Hu, H. C.; Liu, Y. H.; Li, B. L.; Cui, Z. S.; Zhang, Z. H. RSC Adv. 2015, 5, 7720.
[23] Ma, C. T.; Liu, P.; Wu, W.; Zhang, Z. H. J. Mol. Liq. 2017, 242, 606.
[24] Gadilohar, B. L.; Kumbhar, H. S.; Shankarling, G. S. Ind. Eng. Chem. Res. 2014, 53, 19010.
[25] Wang, P.; Ma, F. P.; Zhang, Z. H. J. Mol. Liq. 2014, 198, 259.
[26] Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K. Chem. Eur. J. 2004, 10. 3769.
[27] Carriazo, D.; Gutiérrez, M. C.; Ferrer, M. L.; Del, M. F. Chem. Mater. 2010, 22, 2711.
[28] Ai, F.; Xie, Z. B.; Jiang, G. F.; Ji, J. J.; Le, Z. G. Chin. J. Org. Chem. 2018, 38, 2174(in Chinese). (艾锋, 谢宗波, 姜国芳, 季久健, 乐长高, 有机化学, 2018, 38, 2174.)
[29] Abbott, A. P.; Capper, G.; Davies, D. L.; Kenzie, K. J.; Obi, S. U. J. Chem. Eng. Data 2006, 51, 1280.
[30] Maugeri, Z.; Leitner, W.; María, P. D. Tetrahedron Lett. 2012, 53, 6968.
[31] Wang, A. L.; Zheng, X. L.; Zhao, Z. Z.; Li, Z. P.; Zheng, X. F. Prog. Chem. 2014, 26, 784(in Chinese). (王爱玲, 郑学良, 赵壮志, 李长平, 郑学仿, 化学进展, 2014, 26, 784.)
[32] Zhong, M. B.; Sun, S.; Cheng, J.; Shao, Y. J. Org. Chem. 2016, 81, 10825.
[33] Ren, X. X.; Han, S. J.; Gao, X. Y.; Li, J. Y.; Zou, D. P.; Wu, Y. J.; Wu, Y. S. Tetrahedron Lett. 2018, 59, 1065.
Options
Outlines

/

〈 〉