I2-promoted direct one-pot synthesis of 2-aryl-3-(pyridine-2- ylamino)imidazo[1,2-a]pyridines from aromatic ketones and 2-aminopyridines

Tetrahedron Letters

Volumn 54, Issue 10, 2013, Pages 1222-1226

  Fei, Zhuan ^a   Zhu, Yan Ping ^a   Liu, Mei Cai ^a   Jia, Feng Cheng ^a   Wu, An Xin ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

Aromatic ketones; Heterocyclization; Imidazo 1,2 a pyridines; One pot

Indexed keywords

2 AMINOPYRIDINE DERIVATIVE; ACETOPHENONE; DIMETHYL SULFOXIDE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; IODINE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; HALOGENATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84873110444     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.12.072     Document Type: Article

References (35)

1. M.H. Wiegand Drugs 68 2008 2411
2. K.S. Gudmundsson, J.D. Williams, J.C. Drach, and L.B. Townsend J. Med. Chem. 46 2003 1449
3. J.J. Kaminsky, and A.M. Doweyko J. Med. Chem. 40 1999 427
4. S.M. Hanson, E.V. Morlock, K.A. Satyshur, and C. Czajkowski J. Med. Chem. 51 2008 7243
5. T.S. Harrison, and G.M. Keating CNS Drugs 19 2005 65
6. E. Kianmehr, M. Ghanbari, M.N. Niri, and R. Faramarzi J. Comb. Chem. 12 2010 41
7. I.V. Seregin, A.W. Schammel, and V. Gevorgyan Org. Lett. 9 2007 3433
8. A.R. Katritzky, Y.J. Xu, and H. Tu J. Org. Chem. 68 2003 4935
9. A. Herath, R. Dahl, and N.D.P. Cosford Org. Lett. 12 2010 412
10. O.N. Burchak, L. Mugherli, M. Ostuni, J.J. Lacapère, and M. Balakirev J. Am. Chem. Soc. 133 2011 10058
11. S.K. Guchhait, A.L. Chandgude, and G. Priyadarshani J. Org. Chem. 77 2011 4438
12. P. Liu, C.L. Deng, X.S. Lei, and G.Q. Lin Eur. J. Org. Chem. 36 2011 7308
13. S. Mishra, and R. Ghosh Synthesis 2011 3463
14. N. Chernyak, and V. Gevorgyan Angew. Chem., Int. Ed. 49 2010 2743
15. R.B. Lacerda, C.K.F. de Lima, L.L. da Siva, N.C. Romeiro, A.L. Miranda, E.J. Barreiro, and C.A.M. Fraga Bioorg. Med. Chem. 17 2009 74 and references therein
16. H. Wang, Y. Wang, C. Peng, J. Zhang, and Q. Zhu J. Am. Chem. Soc. 132 2010 13217
17. R.L. Yan, H. Han, C. Ma, Z.Y. Ren, X.A. Gao, G.S. Huang, and Y.M. Liang J. Org. Chem. 77 2012 2024
18. Q. Liao, L.Y. Zhang, S.T. Li, and C.J. Xi Org. Lett. 13 2011 228
19. H. Cao, H.Y. Zhan, Y.G. Lin, X.L. Lin, Z.D. Du, and H.F. Jiang Org. Lett. 14 2012 1688
20. J. Zeng, Y.J. Tan, M.L. Leow, and X.W. Liu Org. Lett. 14 2012 4386
21. N. Shao, G.X. Pang, C.X. Yan, G.F. Shi, and Y. Cheng J. Org. Chem. 76 2011 7458
22. A.J. Stasyuk, M. Banasiewicz, M.K. Cyrański, and D.T. Gryko J. Org. Chem. 77 2012 5552
23. L.J. Ma, X.P. Wang, W. Yu, and B. Han Chem. Commun. 47 2011 11333
24. X. Wang, L. Ma, and W. Yu Synthesis 2011 2445
25. T.J. Donohoe, M.A. Kabeshov, A.H. Rathi, and I.E.D. Smith Org. Biomol. Chem. 10 2012 1093
26. Y.P. Zhu, M.C. Liu, F.C. Jia, J.J. Yuan, M. Lian, Q.H. Gao, and A.X. Wu Org. Lett. 14 2012 3392
27. Y.P. Zhu, F.C. Jia, M.C. Liu, and A.X. Wu Org. Lett. 14 2012 4414
28. Y.P. Zhu, M. Lian, F.C. Jia, M.C. Liu, J.J. Yuan, Q.H. Gao, and A.X. Wu Chem. Commun. 48 2012 9086
29. V. Zuliani, G. Cocconclli, M. Fantini, C. Ghiron, and M. Rivara J. Org. Chem. 72 2007 4551
30. G.D. Yin, M. Gao, N.F. She, S.L. Hu, A.X. Wu, and Y.J. Pan Synthesis 2007 3113
31. Y.P. Zhu, J.J. Yuan, Q.H. Gao, M. Lian, M.C. Liu, Q. Zhao, and A.X. Wu Chem. Commun. 47 2011 12700
32. Y.P. Zhu, J.J. Yuan, Q. Zhao, M. Lian, Q.H. Gao, M.C. Liu, Y. Yang, and A.X. Wu Tetrahedron 68 2012 173
33. M. Lamani, and K.R. Prabhu Chem. Eur. J. 18 2012 14638
34. N. Kornblum, J.W. Powers, G.J. Anderson, W.J. Jones, H.O. Larson, O. Levand, and W.M. Weaver J. Am. Chem. Soc. 79 1957 6562
35. B. Alcaide, R. Pérez-Ossorio, J. Plumet, and M.A. Sierra Tetrahedron Lett. 27 1986 1627