Three novel sequential reactions for the facile synthesis of a library of bisheterocycles possessing the 3-aminoimidazo[1,2- a ]pyridine core catalyzed by bismuth(III) chloride

Synlett

Volumn 24, Issue 5, 2013, Pages 595-602

  Shahrisa, Aziz ^a   Esmati, Somayeh ^a  

^a UNIVERSITY OF TABRIZ   (Iran)

Author keywords

1,4 penylene bisheterocyclic compounds; bismuth(III) chloride; Groebke Blackburn Bienaym reaction; sequential reactions; solvent free reactions; Ugi azide reaction

Indexed keywords

3 AMINOIMIDAZO[1,2 A]PYRIDINE DERIVATIVE; BISMUTH CHLORIDE; BISMUTH DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GROEBKE BLACKBURN BIENAYME REACTION; HANTZSCH REACTION; ONE POT SYNTHESIS; POLYMERIZATION; REACTION TIME; SEQUENTIAL REACTION; TEMPERATURE SENSITIVITY; UGI AZIDE REACTION;

EID: 84874386841     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1318221     Document Type: Article

References (64)

1. Orru, R. V. A.; Ruijter, E. Synthesis of Heterocycles via Multicomponent Reactions; Springer Verlag: Berlin, 2010.
2. Lygin, A. V.; de Meijere, A. Angew. Chem. Int. Ed. 2010, 49, 9094.
3. Sadjadi, S.; Heravi, M. M. Tetrahedron 2011, 67, 2707.
4. Eckert, H. Molecules 2012, 17, 1074.
5. Zou, Y.; Hu, Y.; Liu, H.; Shi, D. ACS Comb. Sci. 2011, 14, 38.
6. Pellegatti, L.; Vedrenne, E.; Hiebel, M. A.; Buron, F.; Massip, S.; Leger, J. M.; Jarry, C.; Routier, S. Tetrahedron Lett. 2011, 52, 5224.
7. Akritopoulou-Zanze, I.; Wakefield, B. D.; Gasiecki, A.; Kalvin, D.; Johnson, E. F.; Kovar, P.; Djuric, S. W. Bioorg. Med. Chem. Lett. 2011, 21, 1480.
8. Guntreddi, T.; Allam, B. K.; Singh, K. N. Synlett 2012, 23, 2635.
9. Sanger, D. J.; Depoortere, H. CNS Drug Rev. 1998, 4, 323.
10. Warner, G. T.; Jarvis, B. Drugs 2002, 62, 1345.
11. Wellington, K.; Scott, L. J. Drugs 2003, 63, 2613.
12. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.
13. Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254.
14. Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
15. Blackburn, C. A. Tetrahedron Lett. 1998, 39, 5469.
16. Bienayme, H.; Bouzid, K. Angew. Chem. Int. Ed. 1998, 37, 2234.
17. Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170.
18. Rival, Y.; Grassy, G.; Taudou, A.; Ecalle, R. Eur. J. Med. Chem. 1991, 26, 13.
19. Fisher, M. H.; Lusi, A. J. Med. Chem. 1972, 15, 982.
20. Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J. C.; Witvrouw, M.; Balzarini, J. J. Med. Chem. 1998, 41, 5108.
21. Ismail, M. A.; Brun, R.; Wenzler, T.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. J. Med. Chem. 2004, 47, 3658.
22. Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8, 305.
23. Langer, S. Z.; Arbilla, S.; Benavides, J.; Scatton, B. Adv. Biochem. Psychopharmacol. 1990, 46, 61.
24. Bode, M. L.; Gravestock, D.; Moleele, S. S.; van der Westhuyzen, C. W.; Pelly, S. C.; Steenkamp, P. A.; Hoppe, H. C.; Khan, T.; Nkabinde, L. A. Bioorg. Med. Chem. 2011, 19, 4227.
25. Dahan-Farkas, N.; Langley, C.; Rousseau, A. L.; Yadav, D. B.; Davids, H.; de Koning, C. B. Eur. J. Med. Chem. 2011, 46, 4573.
26. Chen, J. J.; Golebiowski, A.; McClenaghan, J.; Klopfenstein, S. R.; West, L. Tetrahedron Lett. 2001, 42, 2269.
27. Shaabani, A.; Soleimani, E.; Maleki, A.; Moghimi-Rad, J. Synth. Commun. 2008, 38, 1090.
28. Shaabani, A.; Maleki, A.; Moghimi Rad, J.; Soleimani, E. Chem. Pharm. Bull. 2007, 55, 957.
29. Shaabani, A.; Soleimani, E.; Maleki, A. Monatsh. Chem. 2007, 138, 73.
30. Katritzky, A. R.; Xu, Y. J.; Tu, H. J. Org. Chem. 2003, 68, 4935.
31. Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079.
32. Guchhait, S. K.; Madaan, C. Synlett 2009, 628.
33. Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665.
34. Parchinsky, V. Z.; Shuvalova, O.; Ushakova, O.; Kravchenko, D. V.; Krasavin, M. Tetrahedron Lett. 2006, 47, 947.
35. Shaabani, A.; Soleimani, E.; Sarvary, A.; Rezayan, A. H.; Maleki, A. Chin. J. Chem. 2009, 27, 369.
36. Thompson, M. J.; Hurst, J. M.; Chen, B. Synlett 2008, 3183.
37. Shaabani, A.; Soleimani, E.; Malek, A. Tetrahedron Lett. 2006, 47, 3031.
38. Ugi, I.; Meyr, R.; Fetzer, U.; Steinbrückner, C. Angew. Chem. 1959, 71, 386.
39. Ugi, I.; Steinbrückner, C. Angew. Chem. 1960, 72, 267.
40. Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735.
41. Nixey, T.; Kelly, M.; Semin, D.; Hulme, C. Tetrahedron Lett. 2002, 43, 3681.
42. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
43. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
44. Gunawan, S.; Nichol, G.; Hulme, C. Tetrahedron Lett. 2012, 53, 1664.
45. Schaffert, E. S.; Höfner, G.; Wanner, K. T. Bioorg. Med. Chem. 2011, 19, 6492.
46. Gunawan, S.; Keck, K.; Laetsch, A.; Hulme, C. Mol. Divers. 2012, 16, 601.
47. Marcos, C. F.; Marcaccini, S.; Menchi, G.; Pepino, R.; Torroba, T. Tetrahedron Lett. 2008, 49, 149.
48. Evans, C. G.; Gestwicki, J. E. Org. Lett. 2009, 11, 2957.
49. Wang, R.; Liu, Z. Q. J. Org. Chem. 2012, 77, 3952.
50. Mistry, S. R.; Joshi, R. S.; Sahoo, S. K.; Maheria, K. C. Catal. Lett. 2011, 141, 1541.
51. Reddy, M. V.; Jeong, Y. T. Synlett 2012, 23, 2985.
52. Bothwell, J. M.; Krabbe, S. W.; Mohan, R. S. Chem. Soc. Rev. 2011, 40, 4649.
53. Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.
54. Kouznetsov, V. V.; Gómez, C. M. M.; Parada, L. K. L.; Bermudez, J. H.; Méndez, L. Y. V.; Acevedo, A. M. Mol. Divers. 2011, 15, 1007.
55. Suzuki, H.; Matano, Y. Organobismuth Chemistry; Elsevier: Amsterdam, 2001.
56. Attanasi, O. A.; Bartoccini, S.; Favi, G.; Giorgi, G.; Perrulli, F. R.; Santeusanio, S. J. Org. Chem. 2012, 77, 1161.
57. Alizadeh, A.; Rezvanian, A.; Zhu, L. G. J. Org. Chem. 2012, 77, 4385.
58. Balalaie, S.; Bararjanian, M.; Hosseinzadeh, S.; Rominger, F.; Bijanzadeh, H. R.; Wolf, E. Tetrahedron 2011, 67, 7294.
59. Sreejalekshmi, K. G.; Rajasekharan, K. N. Tetrahedron Lett. 2012, 53, 3627.
60. Al-Tel, T. H.; Al-Qawasmeh, R. A.; Voelter, W. Eur. J. Org. Chem. 2010, 29, 5586.
61. Kalinski, C.; Umkehrer, M.; Gonnard, S.; Jäger, N.; Ross, G.; Hiller, W. Tetrahedron Lett. 2006, 47, 2041.
62. Shahrisa, A.; Miri, R.; Esmati, S.; Saraei, M.; Mehdipour, A. R.; Sharifi, M. Med. Chem. Res. 2012, 21, 284.
63. Shahrisa, A.; Esmati, S.; Gholamhosseini Nazari, M. J. Chem. Sci. 2012, 124, 927.
64. Bose, D. S.; Fatima, L.; Mereyala, H. B. J. Org. Chem. 2003, 68, 587.