Browse > Article
http://dx.doi.org/10.5012/jkcs.2017.61.5.299

Diversification of Imidazo[1,2-a]pyridines under Microwave-Assisted Palladium-Catalyzed Suzuki Reaction  

Lee, Jin-Hee (Department of Chemistry, Chungnam National University)
Park, Seung Yeong (Department of Chemistry, Chungnam National University)
Park, Areum (Department of Chemistry, Chungnam National University)
Yum, Eul Kgun (Department of Chemistry, Chungnam National University)
Publication Information
Keywords
Microwave; Palladium; Suzuki reaction; Aryl coupling; Bromoimidazo[1,2-a]pyridines;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (a) Katritziky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry I, Vol. 5, Pergamon Press, UK, 1984, p 6071.
2 (b) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed., WILEY, UK, 2010, p 373.
3 (c) Couty, F.; Evano, G. Comprehensive Heterocyclic Chemistry III, 3th ed. Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. Elsevier, Oxford, 2008, vol. 11, p 409.
4 (a) Enguehard-Gueiffier, C.; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888   DOI
5 (b) Nair, D. K.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4580.   DOI
6 (a) Swaninston, H. T.; Keating, G. M. CNS Drugs 2005, 19, 65.   DOI
7 (b) Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8, 305.   DOI
8 (c) Ueda, T.; Mizushige, K. Curr. Vasc. Pharmacol. 2006, 4, 1.   DOI
9 (a) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170.   DOI
10 (b) Revankar, G. R.; Matthews, J. R.; Robins, R. K. J. Med. Chem. 1975, 18, 1253.   DOI
11 (a) Elhakmoui, A.; Gueiffier, A.; Milhavet, J. C.; Blache, Y.; Chapat, J. P. Bioorg. Med. Chem. Lett. 1994, 4, 1937.   DOI
12 (b) Gueiffier, A.; Lhassani, M.; Elhakmoui, A.; Snoeck, R.; Andrei, G.; Chavignion, O.; Teulade, J. C.; Kerbal, A.; Essassi, M.; Debouzy, J. C.; Witurowo, J. P.; Blache, Y.; Balzarini, J.; DeClercq, E.; Chapat, J. P. J. Med. Chem. 1996, 39, 2856.   DOI
13 (c) Lhassani, M.; Chavignion, O.; Chezal, J. M.; Teulade, J. C.; Chapat, J. P.; Snoeck, R.; Andrei, G.; Balzarini, J.; DeClercq, E.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271.   DOI
14 (d) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.   DOI
15 (e) Gudmundsson, K. S.; Williams, J. D.; Drach, J. C.; Townsend, L. J. Med. Chem. 2003, 46, 1449.   DOI
16 (a) Scribber, A.; Dennis, R.; Lee, S.; Ouvry, G.; Perrey, D.; Fisher, M.; Wyvratt, M.; Liberator, P.; Gurnett, A.; Brown, C.; Mathew, J.; Thomson, D.; Schmatz, D.; Biftu, T. European Journal of Medical Chemistry 2008, 43, 1123.   DOI
17 (b) Scribber, A.; Dennis, R.; Hong, S. J.; Lee, S.; McIntyre, D.; Perrey, D.; Feng, D.; Fisher, M.; Wyvratt, M.; Leavitt, P.; Liberator, P.; Gurnett, A.; Brown, C.; Mathew, J.; Thomson, D.; Schmatz, D.; Biftu, T. European Journal of Medical Chemistry 2008, 43, 1334.
18 Feng, S.; Hong, D.; Wang, B; Zheng, X.; Miao, K.; Wang, L.; Yun, H.; Gao, L.; Zhao, S.; Shen, H. C. ACS Med. Chem. Lett. 2015, 6, 359.   DOI
19 (a) Kamal, A.; Reddy, J. S.; Ramaiah, M. J.; Dastagiri, D.; Bharathi, E. V.; Sasar, M. V. P.; Pushpavalli, S. N. C. V. L.; Ray, P.; Pal-Bhadra, M. Med. Chem. Commum. 2010, 1, 355.   DOI
20 (b) Vilchis-Reyes, M. A.; Zentella, A.; Martinez- Urbina, M. A.; Guzman, A.; Vargas, O.; Apan, M. T. R.; Gallegos, J. L. V.; Diaz, E. European Journal of Medical Chemistry 2010, 45, 379.   DOI
21 (c) Vilchis-Reyes, M. A.; Zentella, A.; Martinez-Urbina, M. A.; Guzman, A.; Vargas, O.; Apan, M. T. R.; Gallegos, J. L. V.; Diaz, E. European Journal of Medical Chemistry 2010, 45, 379.   DOI
22 (d) Kim, Y. B.; Kang, C. W.; Ranatunga, S.; Yang, H.; Sebti, S. M.; Del Valle, J. R. Bioorg. Med. Chem. Lett. 2014, 24, 4650.   DOI
23 (a) Cao, H.; Liu, X.; Liao, J.; Huang, J.; Qiu, H.; Chen, Q.; Chen, Y. J. Org. Chem. 2014, 79, 11209.   DOI
24 (a) Kazzouli, S. E.; Berteina-Raboin, S.; Mouaddib, A.; Guillaumet, G. Letters in Organic Chemistry, 2012, 9, 118.   DOI
25 (b) Koubachi, J.; Kazzouli, S. E.; Bousmina, M.; Guillaumet, G. Eur. J. Org. Chem. 2014, 5119.
26 (c) Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555.   DOI
27 (b) Yu, J.; Jin, Y.; Zhang, H.; Yang, X.; Fu, H. Chem. Eur. J. 2013, 19, 16804.   DOI
28 (c) Wang, S.; Liu, W.; Cen, J.; Huang, J.; Zhan, H. Tetrahedron Lett. 2014, 55, 1589.   DOI
29 (d) Masurier, N.; Aruta, R.; Gaumet, V.; Denoyelle, S.; Moreau, E.; Lisowski, V.; Martinez, J.; Maillard, L. T. J. Org. Chem. 2012, 77, 3679.   DOI
30 (e) Tachikawa, Y.; Nagasawa, Y.; Furuhashi, S.; Cui, L.; Yamaguchi, E.; Tada, N.; Miura, T.; Itoh, A. RSV Adv. 2015, 5, 5951.   DOI
31 (f) Dimauro, E. F.; Kennedy, J. M. J. Org. Chem. 2007, 72, 1013.   DOI
32 (g) Crozet, M. D.; Castera-Ducros, C.; Vanelle, P. Tetraheron Lett 2006, 47, 7061.   DOI
33 (h) Koubachi, J.; Kazzoli, S. E.; Berteina-Raboin, S.; Mouaddib, A.; Guillaumet, G. J. Org. Chem. 2007, 72, 7650.   DOI
34 (a) Larhed, M. Microwaves in Organic Synthesis, Second ed.,Wiley-VCH, Velog GmbH & Co. KGaA, Weinheim, 2006.
35 (b) Kappe, C. O.; Dallinger, D.; Murphree, S. S. Practical, Microwave Synthesis for Organic Chemists, Wiley-VCH, Velog GmbH& Co. KGaA, Weinheim, 2009.
36 (c) Kappe, C. O. Chem. Soc. Rev. 2008, 37, 1127.   DOI
37 (c) Suh, J. H.; Kang, H. S.; Kim, J. E.; Yum, E. K. Bull. Korean Chem. Soc. 2012, 33, 2067.   DOI
38 (d) Gawande, M. B.; Shelke, S. N.; Zboril, R.; Verma, R. S. Acc. Chem. Res. 2014, 47, 1338.   DOI
39 (a) Kwon, J. K.; Cho, J. H.; Ryu, Y. S.; Oh, S. H.; Yum, E. K. Tetrahedron 2011, 67, 4820.   DOI
40 (b) Kim, S. K.; Kim, J.-H.; Park, Y. C.; Kim, J. W.; Yum, E. K. Tetrahedron 2013, 69,
41 (d) Kwon, J. K.; Lee, J. H.; Kim, T. S.; Yum, E. K. Bull. Korean Chem. Soc. 2016, 37, 1927.   DOI
42 Cao, H.; Zhan, H.; Lin, Y.; Lin, X.; Du, Z.; Jiang, H. Org Lett. 2012, 14, 1688.   DOI