Citation: Hu Hui, Hu Xiaoping, Chen Ming, Sun Ning, Liu Yuanhong. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 190-199. doi: 10.6023/cjoc201708046 shu

Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds

Hu Hui ^† ,
Hu Xiaoping ^† ,
Chen Ming ,
Sun Ning ^, ,
Liu Yuanhong ^,

State Key Laboratory of Organometallic Chemistry, Shanghai Inistitute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Sun Ning, sunning@sioc.ac.cn Liu Yuanhong, yhliu@sioc.ac.cn

^†

Received Date: 23 August 2017
Revised Date: 25 September 2017
Available Online: 29 January 2017
Fund Project: Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000National Natural Science Foundation of China 21572256Project supported by the National Natural Science Foundation of China (Nos. 21572256, 21372244, 21421091), the National Key R&D Program of China (No.2016YFA0202900) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000)National Key R&D Program of China 2016YFA0202900National Natural Science Foundation of China 21421091National Natural Science Foundation of China 21372244

Figures(4)

A gold-catalyzed oxidative ring expansion of 1-alkynyl-1, 2-dihydrophthalazines has been developed. The reaction was catalyzed by PPh₃AuNTf₂in the presence of 8-methylquinoline N-oxide as the oxidant, leading to 2, 3-benzodiazepine derivatives with high efficiency. The reaction likely proceeds through the formation of α-carbonyl gold carbene and 1, 2-migration of a phenyl group, while no 1, 2-H and 1, 2-N migration take place. Further transformation of 2, 3-benzodiazepine products in the presence of FeCl₃ was also carried out, pyrazole and polyfused heterocycle were formed, respectively, through variation of the amounts of FeCl₃.
- gold catalysis,
- oxidation,
- ring expansion,
- 2, 3-benzodiazepine
1. [1]
  (a) Pellow, S.; File, S. E. Pharmacol., Biochem. Behav. 1986, 24, 525.
  (b) Chimirri, A.; De Sarro, G.; De Sarro, A.; Gitto, R.; Grasso, S.; Quartarone, S.; Zappalá, M.; Giusti, P.; Libri, V.; Constanti, A.; Chapman, A. G. J. Med. Chem. 1997, 40, 1258.
  (c) Zappalá, M.; Grasso, S.; Micale, N.; Polimeni, S.; De Micheli, C. Mini-Rev. Med. Chem. 2001, 1, 243.
2. [2]
  Sólyyom, S.; Tarnawa, I. Curr. Pharm. Design 2002, 913.
3. [3]
  Howes, J. F.; Bell, C. Neurotherapeutics 2007, 4, 126. doi: 10.1016/j.nurt.2006.11.001
4. [4]
  Csuzdi, E.; Migléczi, K.; Hazai, I.; Berzsenyi, P.; Pallagi, I. Bioorg. Med. Chem. Lett. 2005, 15, 4662. doi: 10.1016/j.bmcl.2005.07.080
5. [5]
  (a) Archer, G. A.; Sternbach, L. H. Chem. Rev. 1968, 68, 747.
  (b) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
6. [6]
  (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A. Org. Lett. 2016, 18, 3511.
  (b) Guo, P.; Zeng, X.; Chen, S.; Luo, M. J. Organomet. Chem. 2014, 751, 438.
7. [7]
  (a) Snieckus, V.; Streith, J. Acc. Chem. Res. 1981, 14, 348.
  (b) Sugimoto, K.; Hayashi, R.; Nemoto, H.; Toyooka, N.; Matsuya, Y. Org. Lett. 2012, 14, 3510.
  (c) Guo, C.; Sahoo, B.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17402.
  (d) Li, Z.; Yu, H.; Feng, Y.; Hou, Z.; Zhang, L.; Yang, W.; Wu, Y.; Xiao, Y.; Guo, H. RSC Adv. 2015, 5, 34481.
8. [8]
  (a) Horváth, E. J.; Horváth, K.; Hámori, T.; Fekete, M. I. K.; Sólyom, S.; Palkovits, M. Prog. Neurobiol. 2000, 60, 309.
  (b) Okuma, K.; Tanabe, Y.; Nagahora, N.; Shioji, K. Bull. Chem. Soc. Jpn. 2015, 88, 1064.
  (c) Chan, C.-K.; Tsai, Y.-L.; Chan, Y.-L.; Chang, M.-Y. J. Org. Chem. 2016, 81, 9836.
  (d) Wang, J.; Wang, L.; Guo, S.; Zha, S.; Zhu, J. Org. Lett. 2017, 19, 3640.
9. [9]
10. [10]
  For recent papers, see:gold-catalyzed ring expansion reactions without oxidant:(a) Markham, J. P.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 9708.
  (b) Kleinbeck, F.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 9178.
  (c) Barluenga, J.; Tudela, E.; Vicente, R.; Ballesteros, A.; Tomás, M. Angew. Chem., Int. Ed. 2011, 50, 2107.
  Diphenylsulfoxide as the oxidant:(d) Witham, C. A.; Mauleόn, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
  (e) Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156.
  Quinoline/pyridine N-oxide as the oxidant:(f) Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258.
  (g) Vasu, D.; Hung, H.-H.; Bhunia, S.; Gawade, S. A.; Das, A.; Liu, R.-S. Angew. Chem., Int. Ed. 2011, 50, 6911.
  (h) Qian, D.; Zhang, J. Chem. Commun. 2011, 47, 11152.
  (i) Yuan, W.; Dong, X.; Wei, Y.; Shi, M. Chem.-Eur. J. 2012, 18, 10501.
  Nitrone as the oxidant:(j) Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040.
  (k) Chen, D.; Song, G.; Jia, A.; Li, X. J. Org. Chem. 2011, 76, 8488.
11. [11]
  Chen. M.; Chen, Y.; Sun, N.; Zhao, J.; Liu, Y; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 1200. doi: 10.1002/anie.201410056
12. [12]
  Chen, M.; Sun, N.; Xu, W.; Zhao, J.; Wang, G.; Liu, Y. Chem.-Eur. J. 2015, 21, 18571. doi: 10.1002/chem.201504165
13. [13]
  Zhao, J.; Liu, J.; Xie, X.; Li, S.; Liu, Y. Org. Lett. 2015, 17, 5926. doi: 10.1021/acs.orglett.5b03160
14. [14]
  Braunstein, P.; Lehner, H.; Matt, D.; Burgess, K.; Ohlmeyer, M. J. Inorg. Synth. 1990, 27, 218.
15. [15]
  Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133. doi: 10.1021/ol0515917
16. [16]
  Henrion, G.; E. J. Chavas, T.; Goff, X. L.; Gagosz, F. Angew. Chem., Int. Ed. 2013, 52, 6277. doi: 10.1002/anie.201301015
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