Citation: Wei Ting, Zeng Yongming, He Wei, Geng Lili, Hong Liang. A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy[J]. Chinese Chemical Letters, ;2019, 30(2): 383-385. doi: 10.1016/j.cclet.2018.03.031 shu

A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy

Wei Ting ^a ,
Zeng Yongming ^a,b,*, ,
He Wei ^a ,
Geng Lili ^a ,
Hong Liang ^a

a.
Department of Chemistry and Applied Chemistry, Changji University, Changji 831100, China
b.
State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China

zym903@126.com

Received Date: 8 February 2018
Revised Date: 16 March 2018
Accepted Date: 26 March 2018
Available Online: 27 February 2018

Figures(4)

A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of α-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course.
- α-Amino ketones,
- N-Bromosuccinimide,
- Alkynes,
- One-pot synthesis
1. [1]
  (a) A.J. Eshleman, K.M. Wolfrum, M.G. Hatfield, et al., Biochem. Pharmacol. 85 (2013) 1803-1815;
  (b) B.E. Blough, A. Landavazo, J.S. Partilla, et al., ACS Med. Chem. Lett. 5 (2014) 623-627;
  (c) S. Guha, V. Rajeshkumar, S.S. Kotha, G. Sekar, Org. Lett. 17 (2015) 406-409;
  (d) R. Kolanos, J.S. Partilla, M.H. Baumann, et al., ACS Chem. Neurosci. 6 (2015) 771-777;
  (e) F.I. Carrol, B.E. Blough, P. Abraham, et al., J. Med. Chem. 52 (2009) 6768-6781;
  (f) K. Cameron, R. Kolanos, R. Verkariya, L.D. Felice, R.A. Glennon, Psychopharmacology 227 (2013) 493-499.
2. [2]
  (a) L. He, J. Pian, J. Shi, G. Du, B. Dai, Tetrahedron 70 (2014) 2400-2405;
  (b) F. Carroll, B. Blough, P. Abraham, et al., J. Med. Chem. 52 (2009) 6768-6781;
  (c) T. Sehl, Z. Maugeri, D. Rother, J. Mol. Catal. B: Enzym. 114 (2015) 65-71;
  (d) L. Frolova, N. Evdokimov, K. Hayden, et al., Org. Lett. 13 (2011) 1118-1121;
  (e) W. Wei, Y. Shao, H. Hu, et al., J. Org. Chem. 77 (2012) 7157-7165.
3. [3]
  (a) P. Selig, Angew. Chem. Int. Ed. 52 (2013) 7080-7082;
  (b) S. Guha, V. Rajeshkumar, S.S. Kotha, G. Sekar, Org. Lett. 17 (2015) 406-409;
  (c) S.L. McDonald, Q. Wang, Chem. Commun. 50 (2014) 2535-2538;
  (d) F.D. Klingler, Acc Chem. Res. 40 (2007) 1367-1376;
  (e) K.A. Dekorver, H. Li, A.G. Lohse, et al., Chem. Rev. 110 (2010) 5064-5106;
  (f) S. Hoffmann, A.M. Seayad, B. List, Angew. Chem. Int. Ed. 44 (2005) 7424-7427;
  (g) G. Li, Y. Liang, J.C. Antilla, J. Am. Chem. Soc. 129 (2007) 5830-5831;
  (h) W. Wen, Y. Zeng, L. Peng, L. Fu, Q. Guo, Org. Lett. 17 (2015) 3922-3925;
  (i) M.R. Smith, K.K. Hii, Chem. Rev. 111 (2011) 1637-1656.
4. [4]
  (a) J. Tatar, R. Markovic, M. Stojanovic, M. Baranac-Stojanovic, Tetrahedron Lett. 51 (2010) 4851-4855;
  (b) K. Morri, Y. Thummala, V.R. Doddi, Org. Lett. 17 (2015) 4640-4643;
  (c) H.Y. Choi, D.Y. Chi, Org. Lett. 5 (2003) 411-414;
  (d) H.Y. Choi, D.Y. Chi, J. Am. Chem. Soc. 123 (2001) 9202-9203;
  (e) C. Wu, X. Xin, Z.M. Fu, et al., Green Chem. 19 (2017) 1983-1989;
  (f) W.M. He, L.Y. Xie, Y.Y. Xu, et al., Org. Biomol. Chem. 10 (2012) 3168-3171;
  (g) L.Y. Xie, Y.D. Wu, W.G. Yi, et al., J. Org. Chem. 18 (2013) 9190-9195;
  (h) Z.W. Chen, D.N. Ye, M. Ye, et al., Tetrahedron Lett. 55 (2014) 1373-1375;
  (i) H.X. Zou, W.B. He, Q.Z. Dong, et al., Eur. J. Org. Chem. 2016 (2016) 116-121.
5. [5]
  (a) G.L. Fisher, R. Burnett, J. Am. Chem. Soc. 137 (2015) 11614-11617;
  (b) Q. Jiang, B. Xu, A. Zhao, et al., J. Org. Chem. 79 (2014) 8750-8756;
  (c) Y. Lv, Y. Li, T. Xiong, et al., Chem. Commun. 50 (2014) 2367-2369;
  (d) J. Majetich, Tetrahedron Lett. 51 (2010) 6830-6834.
6. [6]
  (a) L.H. Huang, X.B. Zhang, Y.H. Zhang, Org. Lett. 4 (2009) 363-366;
  (b) R.L. Gao, C.S. Yi, ACS Catal. 1 (2011) 544-547.
7. [7]
  (a) F. Minisci, R. Galli, Tetrahedron Lett. 5 (1964) 3197-3200;
  (b) J.A. Souto, P.B. Becker, A. Iglesias, K. Muniz, J. Am. Chem. Soc. 134 (2012) 15505-15511;
  (c) T. Miura, T. Bitajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 134 (2012) 194-196;
  (d) T. Sueda, A. Kawada, Y. Urashi, N. Teno, Org. Lett. 15 (2013) 1560-1563;
  (e) R.E. Evans, J.R. Zbieg, S. Zhu, W. Li, D.W.C. Macmillan, J. Am. Chem. Soc. 135 (2013) 16074-16077;
  (f) J.S. Alford, M.L. Davies, Org. Lett. 14 (2012) 6020-6023;
  (g) S. Cacchi, G. Fabrizi, E. Filisti, et al., Org. Biomol. Chem. 10 (2012) 4699-4703.
8. [8]
  (a) M. Li, H. Yuan, B. Zhao, F. Liang, J. Zhang, Chem. Commun. 50 (2014) 2360-2363;
  (b) W. Gao, F. Hu, Y. Huo, et al., Org. Lett. 17 (2015) 3914-3917;
  (c) A. Sakakura, A. Ukai, K. Ishihara, Nature 445 (2007) 900-903;
  (d) Y. Cai, X. Liu, Y. Hui, et al., Angew. Chem. Int. Ed. 49 (2010) 6160-6164;
  (e) S.M. Walter, F. Kniep, E. Herdtweck, S.M. Huber, Angew. Chem. Int. Ed. 50 (2011) 7187-7191;
  (f) M. Ochiai, K. Miyamoto, T. Kaneaki, S. Hayashi, W. Nakanishi, Science 332 (2011) 448-451.
9. [9]
  P.K. Prasad, R.N. Reddi, A. Sudalai, Org. Lett. 18(2016) 500-503. doi: 10.1021/acs.orglett.5b03540
10. [10]
  M.H. Shinde, U.A. Kshirsagar, Org. Biomol. Chem. 14(2016) 858-861. doi: 10.1039/C5OB02034D
11. [11]
  (a) Y. Wei, S. Lin, F. Liang, J. Zhang, Org. Lett. 15 (2013) 852-855;
  (b) Y. Wei, F. Liang, X. Zhang, Org. Lett. 15 (2013) 5186-5189;
  (c) Y. Wei, S. Lin, F. Liang, Org. Lett. 14 (2012) 4202-4205.
12. [12]
  (a) B. Wang, L. Tang, L.Y. Liu, et al., Green Chem. 19 (2017) 5794-5799;
  (b) N. Ren, J. Nie, J.A. Ma, Green Chem. 18 (2016) 6609-6617;
  (c) D.Q. Dong, S.H. Hao, H. Zhang, Z.L. Wang, Chin. Chem. Lett. 28 (2017) 1597-1599.
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