Citation: Lu Lulu, Zhou Bingwei, Jin Hongwei, Liu Yunkui. Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 515-520. doi: 10.6023/cjoc201807025 shu

Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Jin Hongwei, jhwei828@zjut.edu.cn Liu Yunkui, ykuiliu@zjut.edu.cn
Received Date: 16 July 2018
Revised Date: 10 September 2018
Available Online: 14 February 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technologythe National Natural Science Foundation of China 21372201the National Natural Science Foundation of China 21772176

Figures(3)

An 2, 2'-azobis(2-methylpropionitrile) (AIBN) initiated tandem reaction of vinyl azides with isopropylxanthic disulfide to construct C-S/C-N bonds was disclosed. A range of functionalized 6-sulfanylmethyl phenanthridines could be easily accessed in 50%~84% yields with a good regioselectivity. The mechanism study indicates a free radical pathway in this reaction.
- vinyl azides,
- isopropylxanthic disulfide,
- phenanthridine,
- radical reaction
1. [1]
  (a) Keene, B. R. T.; Tissington, P. Adv. Heterocycl. Chem. 1971, 13, 315.
  (b) Bernardo, P. H.; Wan, K. F.; Sivaraman, T.; Xu, J.; Moore, F. K.; Hung, A. W.; Mok, H. Y. K.; Yu, V. C.; Chai, C. L. L. J. Med. Chem. 2008, 51, 6699.
  (c) Zhang, L.; Ang, G. Y.; Chiba, S. Org. Lett. 2010, 12, 3682.
2. [2]
  (a) Cappelli, A.; Anzini, M.; Vomero, S.; Mannuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Bruni, G.; Romeo, M. R.; Menziani, M. C.; Benedetti, P. G.; Langer, T. J. Med. Chem. 1998, 41, 728.
  (b) Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; MacKay, S. P.; Waigh, R. D.; Nabiev, I. Bioorg. Med. Chem. Lett. 2001, 11, 2643.
  (c) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053.
  (d) Cappoen, D.; Claes, P.; Jacobs, J.; Anthonissen, R.; Mathys, V.; Verschaeve, L.; Huygen, K.; Kimpe, N. D. J. Med. Chem. 2014, 57, 2895.
  (e) Naidua, K. M.; Nagesha, H. N.; Singhb, M.; Sriramc, D.; Yogeeswaric, P.; Sekhara, K. V. G. C. Eur. J. Med. Chem. 2015, 92, 415.
  (f) Riddell, I. A.; Johnstone, T. C.; Park, G. Y.; Lippard, S. J. Chem.-Eur. J. 2016, 22, 7574.
3. [3]
  (a) Alonso, R.; Campos, P. J.; García, B.; Rodríguez, M. A. Org. Lett. 2006, 8, 3521.
  (b) Portela-Cubillo, F.; Lymer, J.; Scanlan, E. M.; Scott, J. S.; Walton, J. C. Tetrahedron 2008, 64, 11908.
  (c) McBurney, R. T.; Slawin, A. M. Z.; Smart, L. A.; Yu, Y.; Walton, J. C. Chem. Commun. 2011, 47, 7974.
  (d) McBurney, R. T.; Walton, J. C. J. Am. Chem. Soc. 2013, 135, 7349.
  (e) McBurney, R. T.; Walton, J. C. Beilstein J. Org. Chem. 2013, 9, 1083.
  (f) Jiang, H.; An, X.; Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2015, 54, 4055.
  (g) Hofstra, J. L.; Grassbaugh, B. R.; Tran, Q. M.; Armada, N. R.; de Lijser, H. J. P. J. Org. Chem. 2015, 80, 256.
  (h) Liu, X.; Qing, Z.; Cheng, P.; Zheng, X.; Zeng, J.; Xie, H. Molecules 2016, 21, 1690.
  (i) Tang, J.; Sivaguru, P.; Ning, Y.; Zanoni, G.; Bi, X. Org. Lett. 2017, 19, 4026.
4. [4]
  (a) Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045.
  (b) Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363.
  (c) Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10972.
  (d) Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286.
  (e) Sha, W.; Yu, J.-T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 9179.
  (f) Fang, H.; Zhao, J.; Qian, P.; Han, J.; Pan, Y. Asian J. Org. Chem. 2014, 3, 1266.
  (g) Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z.-W.; Zhou, L. Green Chem. 2014, 16, 2418.
  (h) Fang, H.; Zhao, J. C.; Qian, P.; Han, J. L.; Pan, Y. Asian J. Org. Chem. 2014, 12, 1266.
  (i) Zhang, Z.; Tang, X.; Dolbier, W. R., Jr. Org. Lett. 2015, 17, 4401.
  (j) Lu, S.; Gong, Y.; Zhou, D. J. Org. Chem. 2015, 80, 9336.
  (k) Zhang, H.; Shi, D.; Ren, S.; Jin, H.; Liu, Y. Eur. J. Org. Chem. 2016, 4224.
  (l) Wu, C.; Zhou, Y.; Dong, X.; Qu, J. ARKIOC 2016, 110.
  (m) Yang, Z.; Song, X.; Wei, Z.; Cao, J.; Liang, D.; Duan, H.; Lin, Y. Tetrahedron Lett. 2016, 57, 2410.
  (n) Singh, M.; Yadav, A. K.; Yadav, L. D. S.; Singh, R. K. P. Synlett 2018, 29, 176.
5. [5]
  (a) Wang, Y.-F.; Lonca, G. H.; Runigo, M. L.; Chiba, S. Org. Lett. 2014, 16, 4272.
  (b) Yang, J.-C.; Zhang, J.-J.; Guo, L.-N. Org. Biomol. Chem. 2016, 14, 9806.
  (c) Sun, X.; Yu, S. Chem. Commun. 2016, 52, 10898.
  (d) Mackay, E. G.; Studer, A. Chem. Eur. J. 2016, 22, 13455.
  (e) Mao, L.-L.; Zheng, D.-G.; Zhu, X.-H.; Zhou, A.-X.; Yang, S.-D. Org. Chem. Front. 2018, 5, 232.
  (f) Li, Y.; Zhu, Y.; Yang, S.-D. Org. Chem. Front. 2018, 5, 822.
  (g) Yang, J.-C.; Zhang, J.-Y.; Zhang, J.-J.; Duan, X.-H.; Guo, L.-N. J. Org. Chem. 2018, 83, 1598.
6. [6]
  (a) Casellato, U.; Vidali, M.; Vigato, P. A. Coord. Chem. Rev. 1979, 28, 231.
  (b) Nief, F. Coord. Chem. Rev. 1998, 178.
  (c) Arda, M.; Ozturk, I. I.; Banti, C. N.; Kourkoumelis, N.; Manoli, M.; Tasiopoulos, A. J.; Hadjikakou, S. K. RSC Adv. 2016, 6, 29026.
  (d) Ephritikhine, M. Coor. Chem. Rev. 2016, 319, 35.
  (e) Boreen, M. A.; Parker, B. F.; Hohloch, S.; Skeel, B. A.; Arnold, J. Dalton Trans. 2018, 47, 96.
7. [7]
  (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
  (b) Doroszuk, J.; Musiejuk, M.; Demkowicz, S.; Rachon, J.; Witt, D. RSC Adv. 2016, 6, 105449.
  (c) Jiao, J.; Wei, L.; Ji, X.-M.; Hu, M.-L.; Tang, R.-Y. Adv. Synth. Catal. 2016, 358, 268.
  (d) Dong, Z.-B.; Liu, X.; Bolm, C. Org. Lett. 2017, 19, 5916.
  (e) Cao, Q.; Peng, H.-Y.; Cheng, Y.; Dong, Z.-B. Synthesis 2018, 50, 1527.
8. [8]
  (a) Fuchigami, T.; Chen, C.-S.; Nonaka, T.; Yen, M.-Y.; Tien, H.-J. Bull. Chem. Soc. Jpn. 1986, 59, 487.
  (b) Gueyrard, D.; Tatibouët, A.; Gareau, Y.; Rollin, P. Org. Lett. 1999, 1, 521.
  (c) Enders, D.; Rembiak, A.; Liebich, J. X. Synthesis 2011, 281.
  (d) Camerel, F.; Jeannin, O.; Yzambart, G.; Fabre, B.; Lorcy, D.; Fourmigué, M. New J. Chem. 2013, 37, 992.
  (e) Zhang, L.; Zhu, J.; Ma, J.; Wu, L.; Zhang, W.-H. Org. Lett. 2017, 19, 6308.
9. [9]
  (a) Tan, J.; Guo, Y.; Zeng, F.; Chen, G.; Xie, L.; He, W. Chin. J. Org. Chem. 2018, 38, 1740.
  (b) Wu, C.; Lu, L.-H.; Peng, A.-Z.; Jia, G.-K.; Peng, C.; Cao, Z.; Tang, Z.; He, W.-M.; Xu, X. Green Chem. 2018, 20, 3683.
10. [10]
  (a) Sibbald, P. A.; Michael, F. E. Org. Lett. 2009, 11, 1147.
  (b) Albéniz, A.C.; Espinet, P.; López-Fernández, R.; Sen, A. J. Am. Chem. Soc. 2002, 124, 11278.
11. [11]
  Winterie, J. S.; Mill, T. J. Am. Chem. Soc. 1980, 102, 6336. doi: 10.1021/ja00540a027
12. [12]
  Gareau, Y.; Beauchemin, A. Heterocycles 1998, 48, 2003. doi: 10.3987/COM-98-8230
13. [13]
  Curran, D. P.; Keller, A. J. Am. Chem. Soc. 2006, 128, 13706. doi: 10.1021/ja066077q
14. [14]
  Liu, K.-J.; Jiang, S.; Lu, L.-H.; Tang, L.-L.; Tang, S.-S.; Tang, H.-S.; Tang, Z.; He, W.-M.; Xu, X. Green Chem. 2018, 20, 3038. doi: 10.1039/C8GC00223A
1. [1]
  Shan Wang , Ya-Jian Hu , Xuan Deng , Guang-Yi Zhang , Zichen Xu , Yu-Tao He . Visible light-mediated syntheses of β-pyridyl azides via three-component radical relay. Chinese Chemical Letters, 2026, 37(4): 111276-. doi: 10.1016/j.cclet.2025.111276
2. [2]
  Yanhui Lu , Chengang Pei , Wenqiang Li , Qing Liu , Huan Pang , Xu Yu . Tailoring active sites of cerium and nitrogen Co-doped rhenium disulfide for enhanced hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(12): 111646-. doi: 10.1016/j.cclet.2025.111646
3. [3]
  Si-Fu Gao , Qiang-Qiang Li , Xing Li , Zi-Qiang Zhang , Huanan Huang , Jun Xuan . Rational design of phenanthridine-based AIEgens for organelle-specific imaging: A dual-functional strategy via free amine modulation and carbon-insertion π-extension. Chinese Chemical Letters, 2026, 37(6): 111519-. doi: 10.1016/j.cclet.2025.111519
4. [4]
  Kuanhong Cao , Sainan Chu , Yuanhua Ding , Shanming Lu , Lei Yu , Juan Du . Sustainable Se/C catalysts from carbohydrates: Unlocking oxidative deoximation reaction with high turnover numbers via free radical mechanisms. Chinese Chemical Letters, 2026, 37(1): 111486-. doi: 10.1016/j.cclet.2025.111486
5. [5]
  Da-Qiu Cui , Quan-Xin Li , Jia-Bo Huang , Ying-Qi Zhang , Xuan Wang , Shao-Fei Ni , Long-Wu Ye , Bo Zhou . Atroposelective transformation of vinyl cations by chiral Brønsted acid catalysis. Chinese Chemical Letters, 2026, 37(6): 111738-. doi: 10.1016/j.cclet.2025.111738
6. [6]
  Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
7. [7]
  Nianhua Luo , Jiayi Jiang , Muhammad Suleman , Zhaowen Liu , Shuping Huang , Wei Xiao , Jie Wu , Jiapian Huang . Advances in radical Smiles rearrangement. Chinese Chemical Letters, 2026, 37(2): 111556-. doi: 10.1016/j.cclet.2025.111556
8. [8]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
9. [9]
  Jingrong Huang , Xin Ding , Zihan Lin , Yu Lin , Yongqi Liao , Wang Gu , Fa-Jie Chen , Fen-Er Chen . Bromo nitrile oxide-mediated disulfide formation and capping of N-terminal cysteine in peptides. Chinese Chemical Letters, 2026, 37(6): 111715-. doi: 10.1016/j.cclet.2025.111715
10. [10]
  Cong-Bin Ji , Ding-Xiong Xie , Mei Chen , Ye-Ying Lan , Bao-Hua Zhang , Ji-Ying Yang , Zheng-Hui Kang , Shu-Jie Chen , Yu-Wei Zhang , Yun-Lin Liu . Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation. Chinese Chemical Letters, 2025, 36(7): 110598-. doi: 10.1016/j.cclet.2024.110598
11. [11]
  Tianzhu Qin , Weiwei Zi . Palladium-catalyzed enantioselective [2σ + 2π] cycloadditions of vinyl-carbonyl-bicyclo[1.1.0]butanes with arylidenemalononitriles. Chinese Chemical Letters, 2026, 37(1): 111072-. doi: 10.1016/j.cclet.2025.111072
12. [12]
  Yu Liu , Lan Bao , Xiang Lyu , Zhonglin Wang , Zhengrun Chen , Jinhuan Dong , Xianxiu Xu , Zhongyan Hu . Divergent reactions of indolyl vinyl isonitriles: A facile access to skeletally diverse carboline-based biheteroaryls. Chinese Chemical Letters, 2026, 37(9): 112201-. doi: 10.1016/j.cclet.2025.112201
13. [13]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
14. [14]
  Ping Wang , Ting Wang , Ming Xu , Ze Gao , Hongyu Li , Bowen Li , Yuqi Wang , Chaoqun Qu , Ming Feng . Keplerate polyoxomolybdate nanoball mediated controllable preparation of metal-doped molybdenum disulfide for electrocatalytic hydrogen evolution in acidic and alkaline media. Chinese Chemical Letters, 2024, 35(7): 108930-. doi: 10.1016/j.cclet.2023.108930
15. [15]
  Yalan Deng , Yaqi Wu , Haipeng Xiao , Nuowen Ma , Huifang Miao , Liuxuan Cao , Wei Guo . Synergistic phenol degradation via electron beam irradiation and bimetallic catalysis: Coupling radical and non-radical pathways. Chinese Chemical Letters, 2026, 37(9): 111568-. doi: 10.1016/j.cclet.2025.111568
16. [16]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
17. [17]
  Huai-Gui Li , Can-Ming Zhu , Weidong Yuan , Hongyi Chen , Zhengyuan Bo , Chao Deng , Yingguang Zhu , Kang Chen , Qing-Yuan Meng . Stereodivergent reductive C(sp²)-C(sp³) coupling between cycloketone oximes and vinyl halides enabled by tunable photoredox/Ti dual catalysis. Chinese Chemical Letters, 2026, 37(7): 111941-. doi: 10.1016/j.cclet.2025.111941
18. [18]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
19. [19]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
20. [20]
  Hong-Qiang Dong , Shang-Bo Yu , Shu-Meng Wang , Jia-Hao Zhao , Xu-Guan Bai , Shi-Xing Lei , Zhen-Nan Tian , Jia Tian , Kang-Da Zhang , Lu Wang , Zhan-Ting Li , Shigui Chen . Construction of radical halogen-bonded organic frameworks with enhanced magnetism and conductivity. Chinese Chemical Letters, 2025, 36(8): 110730-. doi: 10.1016/j.cclet.2024.110730

Get Citation

PDF

XML

Metrics

PDF Downloads(13)
Abstract views(1597)
HTML views(118)

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