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
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