Synthesis of novel 6-(substituted benzyl)imidazo[2,1-b][1,3]thiazole catalyzed by polystyrene-supported palladium(II) ethylenediamine complex

Journal of the Brazilian Chemical Society

Volumn 20, Issue 5, 2009, Pages 907-912

  Bakherad, Mohammad ^a   Keivanloo, Ali ^a   Bahramian, Bahram ^a   Kamali, Taghi A ^a  

^a SHAHROOD UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Aryl iodides; Heterogeneous catalyst; Imidazothiazoles; Sonogashira coupling

Indexed keywords

EID: 69049083803     PISSN: 01035053     EISSN: 16784790     Source Type: Journal    
DOI: 10.1590/S0103-50532009000500015     Document Type: Article

References (54)

1. Moore, J. S.; Acc. Chem. Res. 1997, 30, 402
2. Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., eds.; Wiley-VCH: Weinheim, 1998, ch. 10
3. Sonogashira, K.; J. Organomet. Chem. 2002, 653, 46
4. Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., ed.; Wiley-VCH: New York, 2002
5. Tykwinski, R. R.; Angew. Chem., Int. Ed. 2003, 42, 1566
6. Negishi, E.-J.; Anastasia, L.; Chem. Rev. 2003, 103, 1979.
7. Acetylene Chemistry; Stang, P. J.; Diederich, F.; Tykwinski, R. R., eds.; VCH: Weinheim, 2004, ch. 2
8. Modern Arene Chemistry; Astruc, D., ed.; Wiley-VCH: Weinheim, 2002, ch. 6.
9. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D.; Applications of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1988, ch. 10
10. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; Wiley-VCH: Weinheim, 1996, pp. 582
11. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K.; Tetrahedron Lett. 1996, 37, 7445
12. Miller, M. W.; Johnson, C. R.; J. Org. Chem. 1997, 62, 1582
13. Sakai, A.; Aoyama, T.; Shioiri, T.; Tetrahedron Lett. 1999, 40, 4211
14. Yoshimura, F.; Kawata, S.; Hirama, M.; Tetrahedron Lett. 1999, 40, 8281
15. Toyota, M.; Komori, C.; Ihara, M.; J. Org. Chem. 2000, 65, 7110
16. Paterson, I.; Davies, R. D. M.; Marquez, R.; Angew. Chem., Int. Ed. 2001, 40, 603
17. Uenishi, J.-I.; Matsui, K.; Ohmiya, H.; J. Organomet. Chem. 2002, 653, 141.
18. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., eds.; Pergamon: New York, 1991; vol. 3, pp. 521-549.
19. Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y.; J. Org. Chem. 2001, 66, 1910.
20. Casalnuovo, A. L.; Calabrese, J. C.; J. Am. Chem. Soc. 1990, 112, 4324
21. Dibowski, H.; Schmidtchen, F. P.; Tetrahedron Lett. 1998, 39, 525
22. Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M.; Tetrahedron Lett. 2000, 41, 5151
23. Bong, D. T.; Ghadiri, M. R.; Org. Lett. 2001, 3, 2509
24. Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A.; Org. Lett. 2002, 4, 3199
25. Remmele, H.; Köllhofer, A.; Plenio, H.; Organometallics 2003, 22, 4098.
26. Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I.; Org. Lett. 2002, 4, 1691.
27. Okita, T.; Isobe, M.; Synlett 1994, 589
28. Nguefack, J.-F.; Bolitt, V.; Sinou, D.; Tetrahedron Lett. 1996, 37, 5527
29. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C.; Org. Lett. 2000, 2, 1729
30. Netherton, M. R.; Fu, G. C.; Org. Lett. 2001, 3, 4295
31. Mery, D.; Heuzé, K.; Astruc, D.; Chem. Commun. 2003, 1934.
32. Powell, N. A.; Rychnosky, S. D.; Tetrahedron Lett. 1996, 37, 7901
33. Crisp, G. T.; Turner, P. D.; Stephens, K. A.; J. Organomet. Chem. 1998, 570, 219
34. Nakamura, K.; Ohubo, H.; Yamaguchi, M.; Synlett 1999, 549
35. Dai, W.-M.; Guo, D.-S.; Sun, L.-P.; Tetrahedron Lett. 2001, 42, 5275.
36. Uozumi, Y.; Kobayashi, Y.; Heterocycles 2003, 29, 1255
37. Leese, M. P.; Williams, J. M. J.; Synlett 1999, 1645
38. Bergbreiter, D. E.; Liu, Y.-S.; Tetrahedron Lett. 1997, 38, 7843
39. Lin, C.-A.; Luo, F.-T.; Tetrahedron Lett. 2003, 44, 7565
40. Djakovitch, L.; Rollet, P.; Tetrahedron Lett. 2004, 45, 1367
41. Tyrrell, E.; Al-Saardi, A.; Millet, J.; Synlett 2005, 487
42. Gonthier, E.; Breinbauer, R.; Synlett 2003, 1049
43. Novak, Z.; Szabo, A.; Repasi, J.; Kotschy, A.; J. Org. Chem. 2003, 68, 3327.
44. Parlow, J. J.; Mischke, D. A.; Woodard, S. S.; J. Org. Chem. 1997, 62, 5908
45. Valeury, E.; Bradley, M.; Tetrahedron 2007, 63, 8855
46. Mirkhani, V.; Moghadam, M.; Tangestaninejad, S.; Bahramian, B.; Polyhedron 2006, 25, 2904
47. Kang, Q.-X.; Luo, J.-J.; Bai, Y.-B.; Yang, Z.-W.; Lei, Z.-Q.; J. Organomet. Chem. 2005, 690, 6309
48. Chai, L.-T.; Wang, Q.-R.; Tao, F.-G.; J. Mol. Catal. A: Chem. 2007, 276, 137.
49. Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Lenaz, G.; Fato, R.; Bergamini, C.; Farruggia, G.; J. Med. Chem. 2005, 48, 3085
50. Andreani, A.; Rambaldi, M.; Locatelli, A.; Bossa, R.; Fraccari, A.; Galatulas, I.; J. Med. Chem. 1992, 35, 4634
51. Jaguelin, S.; Robert, A.; Gayral, P.; J. Med. Chem. 1991, 26, 51.
52. Yang, Y.-F.; Zhuang, M.; Zeng, C.-X.; Huang, C.-B.; Luo, M.-F.; Chin. J. Chem. 2006, 24, 1309.
53. Sonogashira, K.; Tohda, Y.; Hagihara, N.; Tetrahedron Lett. 1975, 4467.
54. Theron, F; Verry, M; Vessiere, R. In The Chemistry of the Carbon-Carbon Triple Bond, Part I; Patai, S., ed.; J. Wiley & Sons: Chichester, 1978, ch. 10, p. 381.