Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines

doi:10.6023/cjoc201705041

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3198-3203.DOI: 10.6023/cjoc201705041 Previous Articles Next Articles

Articles

无金属催化的8-氨基喹啉C5位上的卤化反应

郝文燕, 王昱赟, 刘云云

江西师范大学化学化工学院南昌 330022

收稿日期:2017-05-28 修回日期:2017-07-18 发布日期:2017-08-30
通讯作者: 郝文燕 E-mail:wenyanhao@jxnu.edu.cn
基金资助:
国家自然科学基金（Nos.21562024，21762023）及江西省教育厅（No.GJJ160285）资助项目.

Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines

Hao Wenyan, Wang Yuyun, Liu Yunyun

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received:2017-05-28 Revised:2017-07-18 Published:2017-08-30
Contact: 10.6023/cjoc201705041 E-mail:wenyanhao@jxnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21562024, 21762023), and the Scientific Research Fund of Jiangxi Provincial Education Department (No. GJJ160285).

1. Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines.PDF(1776KB)

Cite this article

Hao Wenyan, Wang Yuyun, Liu Yunyun. Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines[J]. Chin. J. Org. Chem., 2017, 37(12): 3198-3203.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

[1] (a) Solomon, V. R.; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
(b) Liu, G.; Yi, M.; Liu, L.; Wang, J.; Wang, J. Chem. Commun. 2015, 51, 2911.
[2] Wan, J.; Y. Jing, Y.; Wei, L. Asian J. Org. Chem. 2017, 6, 668.
[3] Gharpure, S. J.; Nanda, S. K.; Adate, P. A.; Shelke, Y. G. J. Org. Chem. 2017, 82, 2067.
[4] Ali, W.; Dahiya, A.; Pandey, R.; Alam, T.; Patel, B. K. J. Org. Chem. 2017, 82, 2089.
[5] Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
[6] Sun, K.; Lv, Y.; Wang, J.; Sun, J.; Liu, L.; Jia, M.; Liu, X.; Z. Li, Z.; Wang, X. Org. Lett. 2015, 17, 4408.
[7] Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
[8] Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525.
[9] (a) Cong, X.; Zeng, X. Org. Lett. 2014, 16, 3716.
(b) Reddy, M. D.; Fronczek, F. R.; Watkins, E. B. Org. Lett. 2016, 18, 5620.
(c) Chen, H.; Li, P.; Wang, M.; Wang, L. Org. Lett. 2016, 18, 4794.
(d) Kuninobu, Y.; Nishia, M.; Kanai, M. Org. Biomol. Chem. 2016, 14, 8092.
(e) Shen, C.; Xu, J.; Beibei Ying, B.; Zhang, P. ChemCatChem 2016, 8, 3557.
(f) Zhang, J.; Hao, X.; Wang, Z.; Ren, C.; Niu, J.; Song, M. Chin. J. Org. Chem. 2017, 37, 1237.
(g) Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805.
[10] (a) Ji, D.; He, X.; Xu, Y.; Xu, Z.; Bian, Y.; Liu, W.; Zhu, Q.; Xu, Y. Org. Lett. 2016, 18, 4478.
(b) Whiteoak, C. J.; Planas, O.; Company, A.; Ribasa, X. Adv. Synth. Catal. 2016, 358, 1679.
(c) He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054.
(d) Dou, Y.; Xie, Z.; Sun, Z.; Fang, H.; Shen, C.; Zhang, P.; Qing Zhu, Q. ChemCatChem 2016, 8, 3570.
(e) Sahoo, H.; Kesava, M.; Ramakrishna, R.; Baidya, M. Chem.-Eur. J. 2016, 22, 1592.
[11] (a) Liang, H.; Jiang, K.; Ding, W.; Yuan, Y.; Shuai, Li.; Chen, Y.; Ye Wei, Y. Chem. Commun. 2015, 51, 16928.
(b) Qiao, H.; Sun, S.; Yang, F.; Zhu, Y.; Zhu, W.; Dong, Y.; Wu, Y.; Kong, X.; Jiang, L.; Wu, Y. Org. Lett. 2015, 17, 6086.
(c) Wei, J.; Jiang, J.; Xiao, X.; Lin, D.; Deng, Y.; Ke, Z.; Jiang, H.; Zeng, W. J. Org. Chem. 2016, 81, 946.
(d) Xu, J.; Shen, C.; Zhu, X.; Zhang, P.; Ajitha, M. J.; Huang, K.; An, Z.; Liu, X. Chem. Asian J. 2016, 11, 882.
(e) Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C.; Yin, S. Org. Lett. 2015, 17, 5528.
[12] (a) Suess, A. M.; Mehmed Z. Ertem, M. Z.; Cramer, C. J. Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
(b) Guo, H.; Chen, M.; Jiang, P.; Chen, J.; Pan, L.; Wang, M.; Xie, C.; Zhang, Y. Tetrahedron 2015, 71, 70.
(c) Liu, X.; Wu, Z.; Luo, X.; He, Y.; Zhou, X.; Fan, Y.; Huang, G. RSC Adv. 2016, 6, 71485.
(d) Xu, J.; Zhu, X.; Zhou, G.; Ying, B.; Ye, P.; Su, L.; Shen, C.; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
(e) Khan, B.; Ruchir Kant, R.; Koley, D. Adv. Synth. Catal. 2016, 358, 2352.
(f) Wu, C.; Zhou, H.; Wu, Q.; He, M.; Li, P.; Su, Q.; Mu, Y. Synlett. 2016, 27, A~H.
(g) Sahoo, H.; Ramakrishna, I.; Baidya, M. Chem. Select 2016, 1, 1949.
(h) He, X.; Xu, Y.; Kong, L.; Wu, H.; Ji, D.; Wang, Z.; Xu, Y.; Zhu, Q. Org. Chem. Front. 2017, 4, 1046.
(i) Rao, N. S.; Reddy, G. M.; Sridhar, B.; Sarma, M. S. Eur. J. Org. Chem. 2017, 438.
[13] Sun, M.; Sun, S.; Qiao, H.; Yang, F.; Zhu, Y.; Kang, J.; Wu, Y.; Wu, Y. Org. Chem. Front. 2016, 3, 1646.
[14] Xia, C.; Wang, K.; Xu, J.; Shen, C.; Sun, D.; Li, H.; Wang, G.; Zhang, P. Org. Biomol. Chem., 2017, 15, 531.
[15] (a) Abouelhassan, Y.; Garrison, V. G.; Burch, M.; Wong, W.; Norwood, V. M.; Huigens, R. W. Bioorg. Med. Chem. Lett. 2014, 24, 5076.
(b) Liu, Y.-C.; Wei, J.-H.; Chen, Z.-F.; Liu, M.; Gu, Y.-Q.; Huang, K.-B.; Li, Z.-Q.; Liang, H. Eur. J. Med. Chem. 2013, 69, 554.
(c) Tardito, S.; Barilli, A.; Bassanetti, I.; Tegoni, M.; Bussolati, O.; Franchi-Gazzola, R.; Mucchino, C.; Marchio, L. J. Med. Chem. 2012, 55, 10448.
(d) Bhat, S.; Shim, J. S.; Zhang, F.; Chong, C. R.; Liu, J. O. Org. Biomol. Chem. 2012, 10, 2979.
(e) Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; Derisi, J. L.; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.
[16] (a) Jiang, H.; Taggart, H.; Zhang, X.; Benbrook, D. M.; Lind, S. E.; Ding, W.-Q. Cancer Lett. 2011, 312, 11.
(b) Heidary, D. K.; Howerton, B. S.; Glazer, E. C. J. Med. Chem. 2014, 57, 8936.
[17] During the preparation of our manuscript, a water-mediated C5-H halogenations of 8-amidoquinolines has been reported. Chen, J.; Wang, T.; Liu, Y.; Wang, T.; Lin, A.; Yao, H.; Xu, J. Org. Chem. Front. 2017, 4, 622.
[18] Hao, W.-Y.; Liu, Y.-Y. Beilstein J. Org. Chem. 2015, 11, 2132.
[19] Menini, L.; da Cruz Santos, J. C.; Gusevskaya, E. V. Adv. Synth. Catal. 2008, 350, 2052.
[20] Wang, Y.; Wang, Y.; Jiang, K.; Zhang, Q.; Li, D. Org. Biomol. Chem. 2016, 14, 10180.
[21] Qiao, H. J.; Sun, S. Y.; Yang, F.; Zhu, Y.; Kang, J. X.; Wu, Y. S.; Wu, Y. J. Adv. Synth. Catal. 20~17, 359, 1976.

无金属催化的8-氨基喹啉C5位上的卤化反应

Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[2]	Jingyi Wang, Jinyu Liu, Dongsheng Chen, Huayan Chen, Xin Xie, Fajun Nan. Design, Synthesis, and Structure-Activity Relationship of Novel Potent and Highly Selective Cysteinyl Leukotriene Receptor 1 (CysLT₁R) Antagonists [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 259-276.
[3]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[4]	Jun Ding, Xiaokun Shi, Yu Hao, Heyuan Bai, Shuyu Zhang. Silver-Catalyzed Enantioselective Intermolecular γ-Amination of β,γ-Unsaturated Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2946-2952.
[5]	Wei Fan. O₂-Enabled C—H Imination of Five-Membered Cyclic Enamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2492-2498.
[6]	Yaxin Liu, Yu Zhang, Shuping Luo. Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2476-2483.
[7]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[8]	Zhou Zhang, Yu Guo, Jing Yang, Dan Wu, Jiaxin Wang, Xinyue Hong, Peijun Cai, Liangce Rong. Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2104-2109.
[9]	Qian Wang, Yuqi Liu, Zongquan Wu. Synthesis and Structure Control of Chiral Helical Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4141-4146.
[10]	Saimi Naibijiang, Lei Zhang, Shalamu Maidina, Jing Zeng, Abudu Rexit Abulikemu. Green Synthesis of Thiosulfonates and Sulfonyl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 236-243.
[11]	Zheng Liu, Jing Yang, Fengwu Liu. New Routes to Antiviral Molnupiravir against SARS-CoV-2 Infection [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2988-2993.
[12]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[13]	Chenyi Cai, Dong Zou. Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1586-1608.
[14]	Tongli Zhang, Jun Yan, Jingli He, Xuezhen Kou, Jiefeng Shen, Delong Liu, Wanbin Zhang. Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1747-1758.
[15]	Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang, Jijiang Wang. Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1843-1848.