Citation: Xiao Genhua, Min Hao, Zheng Zhilei, Deng Guobo, Liang Yun. Copper-catalyzed three-component reaction of imidazo[1, 2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1, 2-a]pyridines[J]. Chinese Chemical Letters, ;2018, 29(9): 1363-1366. doi: 10.1016/j.cclet.2017.12.013 shu

Copper-catalyzed three-component reaction of imidazo[1, 2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1, 2-a]pyridines

National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China

Corresponding author: Deng Guobo, gbdeng@hunnu.edu.cn Liang Yun, yliang@hunnu.edu.cn
Received Date: 7 October 2017
Revised Date: 8 December 2017
Accepted Date: 18 December 2017
Available Online: 20 September 2017

Figures(3)

In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo[1, 2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.
- Copper,
- Three-component,
- Pyridine,
- Sulfur,
- Arylboronic acids
1. [1]
  (a) A. R. Ali, E. R. El-Bendary, M. A. Ghaly, I. A. Shehata, Eur. J. Med. Chem. 75(2014) 492-500;
  (b) Y. Matsuya, Y. Kobayashi, S. Uchida, et al., Bioorg. Med. Chem. Lett. 23(2013) 4907-4910;
  (c) R. Budriesi, P. Ioan, A. Leoni, et al., J. Med. Chem. 54(2011) 3885-3894;
  (d) K. F. Byth, C. G, C. L. Forder, S. E. Oakes, A. P. Thomas, Mol. Cancer Ther. 5(2006) 655-664;
  (e) K. Mizushige, T. Ueda, K. Yukiiri, H. Suzuki, Cardiovasc. Drug Rev. 20(2002) 163-174;
  (f) K. C. Rupert, J. R. Henry, J. H. Dodd, et al., Bioorg. Med. Chem. Lett. 13(2003) 347-350;
  (g) Y. Abe, H. Kayakiri, S. Satoh, et al., J. Med. Chem. 41(1998) 4587-4598.
2. [2]
  (a) T. Okubo, R. Yoshikawa, S. Chaki, S. Okuyamac, A. Nakazatoa, Bioorg. Med. Chem. Lett. 12(2004) 423-438;
  (b) A. Berson, V. Descatoire, A. Sutton, et al., J. Pharmacol. Exp. Ther. 299(2001) 793-800;
  (c) P. G. George, G. Rossey, M. Sevrin, et al., Monogr. Ser. 8(1993) 49-65.
3. [3]
  (a) B. Du, A. Shan, Y. Zhang, et al., Am. J. Med. Sci. 347(2014) 178-182;
  (b) S. M. Hanson, E. V. Morlock, K. A. Satyshur, C. Czajkowski, J. Med. Chem. 51(2008) 7243-7252.
4. [4]
  H. Depoortere, P. George, US 5064836, 1991.
5. [5]
  D.J. Sanger, Behav. Pharmacol. 6(1995) 116-126.
6. [6]
  (a) D. Belohlavek, P. Malfertheiner, Scand. J. Gastroenterol. Suppl. 54(1979) 44;
  (b) L. Almirante, L. Polo, A. Mugnaini, et al., J. Med. Chem. 8(1965) 305-312.
7. [7]
  L.A. Sorbera, J. Castaner, P.A. Leeson, Drugs Future 27(2002) 935-941. doi: 10.1358/dof.2002.027.10.701186
8. [8]
  (a) T. Ueda, K. Mizusgige, K. Yukiiri, T. Takahashi, Cerebrovasc. Dis. 16(2003) 396-401;
  (b) K. Mizushige, T. Ueda, K. Yukiiri, H. Suzuki, Cardiovasc. Drug Rev. 20(2002) 163-174;
  (c) Y. Uemura, S. Tanaka, S. Ida, T. J. Yuzuriha, J. Pharm. Pharmacol. 45(1993) 1077-1081.
9. [9]
  (a) H. Liu, X. Jiang, Chem. Asian J. 8(2013) 2546-2563;
  (b) A. Gangjee, Y. Zeng, T. Talreja, et al., J. Med. Chem. 50(2007) 3046-3053;
  (c) G. De Martino, M. C. Edler, G. La Regina, et al., J. Med. Chem. 49(2006) 947-954;
  (d) A. M. Faucher, P. W. White, C. Brochu, et al., J. Med. Chem. 47(2004) 18-21;
  (e) G. Liu, J. R. Huth, E. T. Olejniczak, et al., J. Med. Chem. 44(2001) 1202-1210;
  (f) C. M. Rayner, Contemp. Org. Synth. 2(1995) 409-440.
10. [10]
  (a) C. Ravi, A. Joshi, S. Adimurthy, Eur. J. Org. Chem. 25(2017) 3646-3651;
  (b) J. Rafique, S. Saba, A. R. Rosário, A. L. Braga, Chem. Eur. J. 22(2016) 1-10;
  (c) Z. Gao, X. Zhu, R. Zhang, RSC Adv. 4(2014) 19891-19895;
  (d) D. C. Mohan, S. N. Rao, C. Ravi, S. Adimurthy, Asian J. Org. Chem. 3(2014) 609-613;
  (e) W. Ge, X. Zhu, Y. Wei, Eur. J. Org. Chem. 2013(2013) 6015-6020;
  (f) Z. Li, J. Hong, X. Zhou, Tetrahedron 67(2011) 3690-3697.
11. [11]
  (a) C. Ravi, D. C. Mohan, S. Adimurthy, Org. Biomol. Chem. 14(2016) 2282-2290;
  (b) Z. Zheng, D. Qi, L. Shi, Catal. Commun. 66(2015) 83-86;
  (c) H. Cao, L. Chen, J. Liu, et al., RSC Adv. 5(2015) 22356-22360;
  (d) M. A. Hiebel, S. Berteina-Raboin, Green Chem. 17(2015) 937-944;
  (e) C. Ravi, D. Chandra Mohan, S. Adimurthy, Org. Lett. 16(2014) 2978-2981.
12. [12]
  (a) W. Q. Wu, Y. N. An, J. X. Li, et al., Org. Chem. Front. 4(2017) 1751-1756;
  (b) X. Huang, S. Wang, B. Li, et al., RSC Adv. 5(2015) 22654-22657.
13. [13]
  C. Ravi, D.C. Mohan, S. Adimurthy, Org. Biomol. Chem. 14(2016) 2282-2290. doi: 10.1039/C5OB02475G
14. [14]
  A.K. Bagdi, S. Mitra, M. Ghosh, A. Hajra, Org. Biomol. Chem. 13(2015) 3314-3320. doi: 10.1039/C5OB00033E
15. [15]
  P.F. Sun, D.S. Yang, W. Wei, et al., Green Chem. 19(2017) 4785-4791. doi: 10.1039/C7GC01891F
16. [16]
  C. Ravi, N.N.K. Reddy, V. Pappula, S. Samanta, S. Adimurthy, J. Org. Chem. 81(2016) 9964-9972. doi: 10.1021/acs.joc.6b01715
17. [17]
  F. Xiao, S. Chen, C. Li, H. Huang, G.J. Deng, Adv. Synth. Catal. 358(2016) 3881-3886. doi: 10.1002/adsc.201600642
18. [18]
  (a) W. H. Zhu, Y. C. Ding, Z. G. Bian, et al., Adv. Synth. Catal. 359(2017) 2215-2221;
  (b) L. Yu, Y. L. Wu, T. Chen, Y. Pan, Q. Xu, Org. Lett. 15(2013) 144-147.
19. [19]
  J. Li, C. Li, S. Yang, et al., J. Org. Chem. 81(2016) 7771-7783. doi: 10.1021/acs.joc.6b01428
20. [20]
  H. Huang, P. Dang, L. Wu, Y. Liang, J. Liu, Tetrahedron Lett. 57(2016) 574-577. doi: 10.1016/j.tetlet.2015.12.091
21. [21]
  (a) J. Xu, L. Zhang, X. Li, et al., Org. Lett 18(2016) 1266-1269;
  (b) J. T. Yu, H. Guo, H. Yi, Y. Jiang, Adv. Synth. Catal. 356(2014) 749-752;
  (c) Z. Li, J. Hong, X. Zhou, Tetrahedron 67(2011) 3690-3697.
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