Citation: Yu Haiyang, Pi Chao, Wang Yong, Cui Xiuling, Wu Yangjie. Iodine-Catalyzed Regioselective Sulfonylation of Quinoline N-Oxides with Sulfonyl Hydrazides[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 124-130. doi: 10.6023/cjoc201709054 shu

Iodine-Catalyzed Regioselective Sulfonylation of Quinoline N-Oxides with Sulfonyl Hydrazides

Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Corresponding author: Cui Xiuling, cuixl@zzu.edu.cn
Received Date: 30 September 2017
Revised Date: 14 November 2017
Available Online: 15 January 2017
Fund Project: the Ministry of Science and Technology of China 2016YFE0132600Project supported by the Ministry of Science and Technology of China (No. 2016YFE0132600) and the Science and Technology Innovation Program of Universities in Henan Province (No. 16HASTIT007)the Science and Technology Innovation Program of Universities in Henan Province 16HASTIT007

Figures(4)

A novel and simple protocol has been developed for the regioselective sulfonylation of quinolone N-oxides at their C-2 postition. This method features with a simple system, high efficiency, environmental friendliness, and metal-free conditions. Aliphatic and aryl sulfonyl hydrazides smoothly undergo sulfonylation with quinoline N-oxides in good yields.
- iodine-catalyzed,
- quinoline N-oxides,
- sulfonyl hydrazides
1. [1]
  (a) Noshi, M. N. ; El-Awa, A. ; Torres, E. ; Fuchs, P. L. J. Am. Chem. Soc. 2007, 129, 11242.
  (b) Julia, M. ; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833.
  (c) Meyers, C. Y. ; Malte, A. M. ; Matthews, W. S. J. Am. Chem. Soc. 1969, 91, 7510.
  (d) Söderman, S. C. ; Schwan, A. L. J. Org. Chem. 2012, 77, 10978.
2. [2]
  (a) Zhang, C. P. ; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183.
  (b) Frankel, B. A. ; Bentley, M. ; Kruger, R. G. ; McCafferty, D. G. J. Am. Chem. Soc. 2004, 126, 3404.
  (c) Williams, T. M. ; Ciccarone, T. M. ; MacTough, S. C. ; Rooney, C. S. ; Balani, S. K. ; Condra, J. H. ; Emini, E. A. ; Goldman, M. E. ; Greenlee, W. J. ; Kauffman, L. R. ; O'Brien, J. A. ; Sardana, V. V. ; Schleif, W. A. ; Theoharides, A. D. ; Anderson, P. S. J. Med. Chem. 1993, 36, 1291.
  (d) Choi-Sledeski, Y. M. ; Kearney, R. ; Poli, G. ; Pauls, H. ; Gardner, C. ; Gong, Y. ; Becker, M. ; Davis, R. ; Spada, A. ; Liang, G. Y. ; Chu, V. ; Brown, K. ; Collussi, D. ; Leadley, R. ; Rebello, J. S. ; Moxey, P. ; Morgan, S. ; Bentley, R. ; Kasiewski, C. ; Maignan, S. ; Guilloteau, J. P. ; Mikol, V. J. Med. Chem. 2003, 46, 681.
  (e) Maignan, S. ; Guilloteau, J. P. ; Choi-Sledeski, Y. M. ; Becker, M. R. ; Ewing, W. R. ; Pauls, H. W. ; Spada, A. P. ; Mikol, V. J. Med. Chem. 2003, 46, 685.
  (f) Wang, G. ; Mahesh, U. ; Chen, G. Y. ; Yao, S. Q. Org. Lett. 2003, 5, 737.
3. [3]
  Sahoo, S. K.; Banerjee, A.; Chakraborty, S.; Patel, B. K. ACS Catal. 2012, 2, 544. doi: 10.1021/cs200590p
4. [4]
  Trankle, W. G.; Kopach, M. E. Org. Process Res. Dev. 2007, 11, 913. doi: 10.1021/op700060e
5. [5]
  (a) Migita, T. ; Shimizu, T. ; Asami, Y. ; Shiobara, J. ; Kato, Y. ; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
  (b) Li, G. Y. Angew. Chem. , Int. Ed. 2001, 40, 1513.
  (c) Fernandez-Rodriguez, M. A. ; Shen, Q. ; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
  (d) Wong, Y. -C. ; Jayanth, T. T. ; Cheng, C. -H. Org. Lett. 2006, 8, 5613.
  (e) Rout, L. ; Sen, T. K. ; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583.
  (f) Correa, A. ; Carril, M. ; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
  (g) Buch-Wald, S. L. ; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586.
  (h) Reddy, V. P. ; Kumar, A. V. ; Swapna, K. ; Rao, K. R. Org. Lett. 2009, 11, 1697.
  (i) Uyeda, C. ; Tan, Y. ; Fu, G. C. ; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 9548.
  (j) Xu, X. -B. ; Liu, J. ; Zhang, J. J. ; Wang, Y. -W. ; Peng, Y. Org. Lett. 2013, 15, 550.
6. [6]
  (a) Kumar, S. ; Engman, L. J. Org. Chem. 2006, 71, 5400.
  (b) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
  (c) Zhang, S. ; Qian, P. ; Zhang, M. ; Hu, M. ; Cheng, J. J. Org. Chem. 2010, 75, 6732.
7. [7]
  Park, N.; Park, K.; Jang, M.; Lee, S. J. Org. Chem. 2011, 76, 4371. doi: 10.1021/jo2007253
8. [8]
  (a) Qiao, H. J. ; Sun, S. Y. ; Yang, F. ; Zhu, Y. ; Zhu, W. G. ; Dong, Y. X. ; Wu, Y. S. ; Kong, X. T. ; Jiang, L. ; Wu, Y. J. Org. Lett. 2015, 17, 6086.
  (b) Rao, W. H. ; Shi, B. F. Org. Lett. 2015, 17, 2784.
  (c) Liu, J. D. ; Yu, L. ; Zhuang, S. B. ; Gui, Q. W. ; Chen, X. ; Wang, W. D. ; Tan, Z. Chem. Commun. 2015, 51, 6418.
  (d) Liang, H. W. ; Jiang, K. ; Ding, W. ; Yuan, Y. ; Shuai, L. ; Chen, Y. C. ; Wei, Y. Chem. Commun. 2015, 51, 16928.
  (e) Ge, B. Y. ; Wang, D. W. ; Dong, W. F. ; Ma, P. M. ; Li, Y. L. ; Ding, Y. Q. Tetrahedron Lett. 2014, 55, 5443.
  (f) Zhang, D. ; Cui, X. L. ; Zhang, Q. Q. ; Wu, Y. J. J. Org. Chem. 2015, 80, 1517.
  (g) Xu, Y. F. ; Liu, P. ; Li, S. L. ; Sun, P. P. J. Org. Chem. 2015, 80, 1269.
9. [9]
  Zhao, X. D.; Dimitrijevic, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466. doi: 10.1021/ja900200g
10. [10]
  Wu, Z. Y.; Song, H. Y.; Cui, X. L.; Pi, C.; Du, W. W.; Wu, Y. J. Org. Lett. 2013, 15, 1270. doi: 10.1021/ol400178k
11. [11]
  Saidi, O.; Marafie, J.; Ledger, A. E.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298. doi: 10.1021/ja208286b
12. [12]
  Sun, K.; Chen, X. L.; Li, X.; Qu, L. B.; Bi, W. Z.; Chen, X.; Ma, H. L.; Zhang, S. T.; Han, B. W.; Zhao, Y. F.; Li, C. J. Chem. Commun. 2015, 51, 12111. doi: 10.1039/C5CC04484G
13. [13]
  (a) Zhao, X.; Zhang, L. P.; Lu, X. Y.; Li, T. J.; Lu, K. J. Org. Chem. 2015, 80, 2918.
  (b) Sun, J.; Qiu, J. K.; Zhu, Y. L.; Guo, C.; Hao, W. J.; Jiang, B.; Tu, S. J. J. Org. Chem. 2015, 80, 8217.
  (c) Zhao, X.; Zhang, L. P.; Li, T. J.; Liu, G. Y.; Wang, H. M.; Lu, K. Chem. Commun. 2014, 50, 13121.
  (d) Kang, X.; Yan, R. L.; Yu, G. Q.; Pang, X. B.; Liu, X. X.; Li, X. L.; Xiang, L. K.; Huang, G. S. J. Org. Chem. 2014, 79, 10605.
  (e) Adiyala, P. R.; Chandrasekhar, D.; Kapure, J. S.; Reddy, C. N.; Maurya, R. A. Beilstein J. Org. Chem. 2014, 10, 2065.
  (f) Mohammed, S.; Vishwakarma, R. A.; Bharate, S. B. J. Org. Chem. 2015, 80, 6915.
  (g) Tang, S.; Liu, K.; Long, Y.; Gao, X. L.; Gao, M.; Lei, A. W. Org. Lett. 2015, 17, 2404.
  (h) Singh, R.; Allam, B. K.; Singh, N.; Kumari, K.; Singh, S. K.; Singh, K. N. Org. Lett. 2015, 17, 2656.
  (i) Guo, S. J.; Wan, G.; Sun, S.; Jiang, Y.; Yu, J. T.; Cheng, J. Chem. Commun. 2015, 51, 5085.
  (j) Sashidhara, K. V.; Palnati, G. R.; Singh, L. R.; Upadhyay, A.; Avula, S. R.; Kumar, A.; Kant, R. Green Chem. 2015, 17, 3766.
  (k) Xiang, L. K.; Niu, Y. N.; Pang, X. B.; Yang, X. D.; Yan, R. L. Chem. Commun. 2015, 51, 6598.
  (l) Parumala, S. K. R.; Peddinti, R. K. Green Chem. 2015, 17, 4068.
  (m) Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757(in Chinese).
  (王丁意, 张荣兴, 林森, 邓瑞华, 严兆华, 有机化学, 2016, 36, 2757.)
  (n) Hu, F.; Gao, W.; Chang, H.; Li, X.; Wei, W. Chin. J. Org. Chem. 2015, 35, 1848(in Chinese).
  (胡飞, 高文超, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1848.)
14. [14]
  Yang, F. L.; Tian, S. K. Angew. Chem., Int. Ed. 2013, 52, 4929. doi: 10.1002/anie.v52.18
15. [15]
  Londregan, A. T.; Burford, K.; Conn, E. L.; Hesp, K. D. Org. Lett. 2014, 16, 3336. doi: 10.1021/ol501359r
16. [16]
  Myers, A. G.; Zheng, B.; and Movassaghi, M. J. Org. Chem. 1997, 62, 7507. doi: 10.1021/jo9710137
17. [17]
  Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2016, 18, 4144. doi: 10.1021/acs.orglett.6b02289
18. [18]
  Su, Y.; Zhou, X.; He, C.; Zhang, W.; Ling, X.; Xiao, X. J. Org. Chem. 2016, 81, 4981. doi: 10.1021/acs.joc.6b00475
1. [1]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
2. [2]
  Lianshun Zhang , Lan Bao , Ting Song , Shangying Qiao , Yifan Liu , Xianxiu Xu , Jinhuan Dong . Cu-catalyzed biheterocyclization along with sulfonyl remote migration: Access to Marinoquinoline alkaloids and 4-sulfonyl pyrrolo[2,3-c]quinolines. Chinese Chemical Letters, 2025, 36(10): 110915-. doi: 10.1016/j.cclet.2025.110915
3. [3]
  Cailing Wu , Shaojie Wu , Qifei Huang , Kai Sun , Xianqiang Huang , Jianji Wang , Bing Yu . Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110250-. doi: 10.1016/j.cclet.2024.110250
4. [4]
  Zhiqian Chang , Xiaochun He , Xuemei Zhang , Zhong Lian . Stereoconvergent synthesis of chiral sulfonyl phthalide containing two chiral centers from Z/E mixed alkenes via copper catalysis. Chinese Chemical Letters, 2026, 37(5): 111405-. doi: 10.1016/j.cclet.2025.111405
5. [5]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
6. [6]
  Huihua GONG , Tianhua CUI , Li JI , Jichuan ZHANG , Liyuan ZHANG , Yan CHEN , Zhenye WANG , Jiaqi XU , Ruixiang LI . Hydrogenation of CO₂ to formate catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated iridium(Ⅰ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2609-2620. doi: 10.11862/CJIC.20250170
7. [7]
  Feng Wu , Yuanjiu Xiao , Mengran Wei , Guoqiang Wang , Jian-Jun Feng . Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes. Chinese Chemical Letters, 2026, 37(3): 111963-. doi: 10.1016/j.cclet.2025.111963
8. [8]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
9. [9]
  Jingyao Yu , Zhuoran Yang , Jian Jiang , Mengshu Xu , Chunyu Yang , Zhuo Li , Wei Guo . Engineering asymmetric electronic structures in Fe-N-S-C nanozymes for dual enzyme-catalyzed-induced ferroptosis and enhanced antitumor efficacy. Chinese Chemical Letters, 2026, 37(3): 111693-. doi: 10.1016/j.cclet.2025.111693
10. [10]
  Cui Xin , Zi-Jian Zhao , Wei-Min He . Indole-quinoline transmutation enabled by a formal rhodium carbynoid. Chinese Chemical Letters, 2025, 36(11): 111583-. doi: 10.1016/j.cclet.2025.111583
11. [11]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
12. [12]
  Chen-Chang Cui , Shao-Qing Shi , Lu-Yao Wang , Feng Lin , Man-Su Tu , Wen-Juan Hao , Bo Jiang . Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation. Chinese Chemical Letters, 2025, 36(6): 110541-. doi: 10.1016/j.cclet.2024.110541
13. [13]
  Yajun Hou , Chuanzheng Zhu , Qiang Wang , Xiaomeng Zhao , Kun Luo , Zongshuai Gong , Zhihao Yuan . ~2.5 nm pores in carbon-based cathode promise better zinc-iodine batteries. Chinese Chemical Letters, 2024, 35(5): 108697-. doi: 10.1016/j.cclet.2023.108697
14. [14]
  Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201
15. [15]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
16. [16]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
17. [17]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383
18. [18]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
19. [19]
  Ting Zhang , Jia Chen , Mingxia Sun , Juanjuan Wang , Lulu Wang , Shuzhe Guan , Hongdeng Qiu . Bis-trimethylammonium pillar[5]arene and biphenyldisulfonic acid-based ionic pair assembled single crystals for iodine adsorption. Chinese Chemical Letters, 2026, 37(5): 111790-. doi: 10.1016/j.cclet.2025.111790
20. [20]
  Yuhan Wu , Qing Zhao , Zhijie Wang . Layered vanadium oxides: Promising cathode materials for calcium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(5): 100271-100271. doi: 10.1016/j.cjsc.2024.100271

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(3128)
HTML views(260)

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