Unprecedented catalytic activity of Fe(NO3)3·9H2O: Regioselective synthesis of 2-nitroimidazopyridines via oxidative amination

Organic Letters

Volumn 16, Issue 17, 2014, Pages 4630-4633

  Monir, Kamarul ^a   Bagdi, Avik Kumar ^a   Ghosh, Monoranjan ^a   Hajra, Alakananda ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA-AMINOPYRIDINE; AMINOPYRIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; IRON; NITRO DERIVATIVE; PYRIDINE DERIVATIVE; STYRENE DERIVATIVE;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKENES; AMINATION; AMINOPYRIDINES; CATALYSIS; IMIDAZOLES; IRON; MOLECULAR STRUCTURE; NITRO COMPOUNDS; OXIDATION-REDUCTION; PYRIDINES; STEREOISOMERISM; STYRENES;

EID: 84910019922     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502218u     Document Type: Article

References (68)

1. Lhassani, M.; Chavignon, O.; Chezal, J. M.; Teulade, J. C.; Chapat, J. P.; Snoeck, R.; Andrei, G.; Balzarini, J.; Clercq, E. D.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271 and the references cited therein
2. Humphries, A. C.; Gancia, E.; Gilligan, M. T.; Goodacre, S.; Hallett, D.; Marchant, K. J.; Thomas, S. R. Bioorg. Med. Chem. Lett. 2006, 16, 1518
3. Fuchs, K.; Romig, M.; Mendla, K.; Briem, H.; Fechteler, K. WO2002014313. Chem. Abstr. 2002, 136, 183824r.
4. Hamdouchi, C.; Blas, J.; de Prado, M.; del Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50
5. Langer, S. Z.; Arbilla, S.; Benavides, J.; Scatton, B. Adv. Biochem. Psychopharmacol. 1990, 46, 61
6. Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drugs Rev. 2002, 20, 163
7. Boerner, R. J.; Moller, H. J. Psychopharmakotherapie 1997, 4, 145
8. Stasyuk, A. J.; Banasiewicz, M.; Cyranski, M. K.; Gryko, D. T. J. Org. Chem. 2012, 77, 5552
9. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743
10. Guchhait, S. K.; Chandgude, A. L.; Priyadarshani, G. J. Org. Chem. 2012, 77, 4438
11. Adib, M.; Sheikhi, E.; Rezaei, N. Tetrahedron Lett. 2011, 52, 3191
12. DiMauro, E. F.; Kennedy, J. M. J. Org. Chem. 2007, 72, 1013
13. Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661
14. Yan, H.; Wang, Y.; Pan, C.; Zhang, H.; Yang, S.; Yan, H.; Wang, Y.; Pan, C.; Zhang, H.; Yang, S.; Ren, X.; Li, J.; Huang, G. Eur. J. Org. Chem. 2014, 2754
15. Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C.; Witvrouw, M.; Balzarini, J.; Clercq, E. D.; Chapat, J.-P. J. Med. Chem. 1998, 41, 5108
16. Hand, E. S.; Paudler, W. W. J. Org. Chem. 1978, 43, 2900
17. Masurier, N.; Moreau, E.; Lartigue, C.; Gaumet, V.; Chezal, J.-M.; Heitz, A.; Teulade, J.-C.; Chavignon, O. J. Org. Chem. 2008, 73, 5989
18. Hamdouchi, C.; Sanchez, C.; Ezquerra, J. Synthesis 1998, 867
19. Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1741
20. Pericherla, K.; Pinku; Khedar, P.; Khungar, B.; Parangband, K.; Kumar, A. RSC Adv. 2013, 3, 18923
21. Mohan, D. C.; Donthiri, R. R.; Rao, S. N.; Adimurthy, S. Adv. Synth. Catal. 2013, 355, 2217
22. Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Adv. Synth. Catal. 2013, 355, 2686
23. He, C.; Hao, J.; Xu, H.; Mo, Y.; Liu, H.; Han, J.; Lei, A. Chem. Commun. 2012, 48, 11073
24. Zeng, J.; Tan, Y. J.; Leow, M. L.; Liu, X.-W. Org. Lett. 2012, 14, 4386
25. Ma, L.; Wang, X.; Yu, W.; Han, B. Chem. Commun. 2011, 47, 11333
26. Monir, K.; Bagdi, A.; Mishra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2014, 356, 1105
27. Wang, H.; Wang, Y.; Liang, D.; Liu, L.; Zhang, J.; Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678
28. Mohan, D. C.; Rao, S. N.; Adimurthy, S. J. Org. Chem. 2013, 78, 1266
29. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217
30. Yan, R.-L.; Yan, H.; Ma, C.; Ren, Z.-Y.; Gao, X.-A.; Huang, G.-S.; Liang, Y.-M. J. Org. Chem. 2012, 77, 2024
31. Yan, H.; Yan, R.; Yang, S.; Gao, X.; Wang, Y.; Huang, G.; Liang, Y. Chem.-Asian J. 2012, 7, 2028
32. Xie, M.-S.; Chu, Z.-L.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. J. Org. Chem. 2014, 79, 1093
33. Santra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1065
34. Desbois, N.; Chezal, J.-M.; Fauvelle, F.; Debouzy, J.-C.; Lartigue, C.; Gueiffier, A.; Blache, Y.; Moreau, E.; Madelmont, J.-C.; Chavignon, O.; Teulade, J.-C. Heterocycles 2005, 65, 1121
35. Rahimizadeh, M.; Pordel, M.; Bakavoli, M.; Eshghi, H. Dyes Pigm. 2010, 86, 266
36. Bolm, C. Nat. Chem. 2009, 1, 420
37. Iron Catalysis in Organic Chemistry; Plietker, B., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
38. Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217
39. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
40. Correa, A.; Mancheño, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
41. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061
42. Czaplik, W. M.; Mayer, M.; Cvengros, J.; Jacobi von Wangelin, A. ChemSusChem 2009, 2, 396
43. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
44. Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591
45. Hatakeyama, T.; Imayoshi, R.; Yoshimoto, Y.; Ghorai, S. K.; Jin, M.; Takaya, H.; Norisuye, K.; Sohrin, Y.; Nakamura, M. J. Am. Chem. Soc. 2012, 134, 20262
46. Naveen, T.; Maity, S.; Sharma, U.; Maiti, D. J. Org. Chem. 2013, 7, 5949
47. Maiti, S.; Biswas, S.; Jana, U. J. Org. Chem. 2010, 75, 1674
48. Chen, M. S.; White, M. C. Science 2007, 318, 783
49. Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844
50. Takacs, J. M.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928
51. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
52. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
53. Rauws, T. R. M.; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463
54. Espino, C. G.; Bois, J. D. Angew. Chem., Int. Ed. 2001, 40, 598
55. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
56. Bois, J. D. Org. Process Res. Dev. 2011, 15, 758
57. Shou, W. G.; Li, J.; Guo, T.; Lin, Z.; Jia, G. Organometallics 2009, 28, 6874
58. Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061
59. Gephart, R. T.; Warren, T. H. Organometallics 2012, 31, 7728
60. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
61. Gu, Q.; Al Mamari, H. H.; Graczyk, K.; Diers, E.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 3868
62. Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7790
63. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851
64. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
65. Zhang, T.; Bao, W. J. Org. Chem. 2013, 78, 1317
66. Maes, J.; Rauws, T. R. M.; Maes, B. U. W. Chem.-Eur. J. 2013, 19, 9137
67. Wang, J.; Hou, J.-T.; Wen, J.; Zhang, J.; Yu, X.-Q. Chem. Commun. 2011, 47, 3652
68. Guan, Z.-H.; Yan, Z.-Y.; Ren, Z.-H.; Liua, X.-Y.; Liang, Y.-M. Chem. Commun. 2010, 46, 2823