Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride

Tetrahedron

Volumn 69, Issue 45, 2013, Pages 9422-9427

  Lu, Yang ^a   Li, Yaming ^a   Zhang, Rong ^a   Jin, Kun ^a   Duan, Chunying ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Aromatic amines; Bismuth nitrate; ortho Nitration; Regioselectivity; Synthetic methods

Indexed keywords

ACETIC ANHYDRIDE; AMIDE; ANILINE DERIVATIVE; BISMUTH NITRATE; N PHENYLCARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NITRATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION OPTIMIZATION; ROOM TEMPERATURE;

EID: 84884674535     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.08.076     Document Type: Article

References (72)

1. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH New York, NY
2. G.A. Olah, R. Malhotra, and S.C. Narang Nitration: Methods and Mechanisms 1989 VCH New York, NY
3. For recent reviews, see: G. Yan, and M. Yang Org. Biomol. Chem. 11 2013 2554
4. K. Smith, S. Almeer, and C. Peters Chem. Commun. 2001 2748
5. G.K.S. Prakash, C. Panja, T. Mathew, V. Surampudi, N.A. Petasis, and G.A. Olah Org. Lett. 6 2004 2205
6. S. Manna, S. Maity, S. Rana, S. Agasti, and D. Maiti Org. Lett. 14 2012 1736
7. X.-F. Wu, J. Schranck, H. Neumann, and M. Beller Chem. Commun. 2011 12462
8. S. Saito, and Y. Koizumi Tetrahedron Lett. 46 2005 4715
9. B.P. Fors, and S.L. Buchwald J. Am. Chem. Soc. 131 2009 12898
10. Y.K. Liu, S.J. Lou, D.Q. Xu, and Z.Y. Xu Chem. - Eur. J. 16 2010 13590
11. W. Zhang, S.J. Lou, Y.K. Liu, and Z.Y. Xu J. Org. Chem. 78 2013 5932
12. L. Zhang, Z. Liu, H. Li, G. Fang, B.-D. Barry, T.A. Belay, X. Bi, and Q. Liu Org. Lett. 13 2011 6536
13. X.H. Yang, C.J. Xi, and Y.F. Jiang Tetrahedron Lett. 46 2005 8781
14. N. Iranpoor, H. Firouzabadi, N. Nowrouzi, and D. Firouzabadi Tetrahedron Lett. 47 2006 6879
15. T.B. Nguyen, L. Ermolenko, and A. Al-Mourabit J. Am. Chem. Soc. 135 2012 118
16. J. Kim, J. Kim, H. Lee, B.M. Lee, and B.H. Kim Tetrahedron 67 2011 8027
17. D. Yang, D. Fokas, J. Li, L. Yu, and C.M. Baldino Synthesis 2005 47
18. D. Cantillo, M. Baghbanzadeh, and C.O. Kappe Angew. Chem., Int. Ed. 51 2012 10190
19. Q. Shi, R. Lu, K. Jin, Z. Zhang, and D. Zhao Green. Chem. 8 2006 868
20. A. Vass, J. Dudas, J. Toth, and R.S. Varma Tetrahedron Lett. 42 2001 5347
21. S. Sana, K. Rajanna, M.M. Ali, and P. Saiprakash Chem. Lett. 29 2000 48
22. Tasneem, M.M. Ali, K.C. Rajanna, and P.K. Saiparakash Synth. Commun. 31 2001 1123
23. M.M.V. Ramana, S.S. Malik, and J.A. Parihar Tetrahedron Lett. 45 2004 8681
24. A.R. Hajipour, and A.E. Ruoho Tetrahedron Lett. 46 2005 8307
25. S.K. Bharadwaj, S. Hussain, M. Kar, and M.K. Chaudhuri Appl. Catal., A 343 2008 62
26. S.K. Bharadwaj, S. Hussain, M. Kar, and M.K. Chaudhuri Catal. Commun. 9 2008 919
27. S. Sana, M.M. Ali, K.C. Rajanna, and P.K. Saiprakash Synth. Commun. 39 2009 2949
28. G. Aridoss, and K.K. Laali J. Org. Chem. 76 2011 8088
29. H. Suzuki, T. Takeuchi, and T. Mori J. Org. Chem. 61 1996 5944
30. P. Strazzolini, G. Verardo, F. Gorassini, and A.G. Giumanini Bull. Chem. Soc. Jpn. 68 1995 1155
31. H. Suzuki, T. Ishibashi, T. Murashima, and K. Tsukamoto Tetrahedron Lett. 32 1991 6591
32. A. Sridhar Rao, P. Srinivas, K. Suresh Babu, and J. Madhusudana Rao Tetrahedron Lett. 46 2005 8141
33. T. Naveen, S. Maity, U. Sharma, and D. Maiti J. Org. Chem. 78 2013 5949
34. T. Taniguchi, and H. Ishibashi Org. Lett. 12 2010 124
35. T. Taniguchi, T. Fujii, and H. Ishibashi Org. Biomol. Chem. 9 2011 653
36. T. Taniguchi, T. Fujii, and H. Ishibashi J. Org. Chem. 75 2010 8126
37. R. Rajagopal, and K.V. Srinivasan Synth. Commun. 33 2003 961
38. A.K. Bose, S.N. Ganguly, M.S. Manhas, S. Rao, J. Speck, U. Pekelny, and E. Pombo-Villars Tetrahedron Lett. 47 2006 1885
39. V. Anuradha, P.V. Srinivas, P. Aparna, and J.M. Rao Tetrahedron Lett. 47 2006 4933
40. M.A. Zolfigol, E. Ghaemi, and E. Madrakian Synth. Commun. 30 2000 1689
41. P.K. Kancharla, Y.S. Reddy, S. Dharuman, and Y.D. Vankar J. Org. Chem. 76 2011 5832
42. N. Nowrouzi, A.M. Mehranpour, E. Bashiri, and Z. Shayan Tetrahedron Lett. 53 2012 4841
43. S.A. Shackelford, M.B. Anderson, L.C. Christie, T. Goetzen, M.C. Guzman, M.A. Hananel, W.D. Kornreich, H.T. Li, V.P. Pathak, A.K. Rabinovich, R.J. Rajapakse, L.K. Truesdale, S.M. Tsank, and H.N. Vazir J. Org. Chem. 68 2003 267
44. For the first example of aniline nitration using bismuth nitrate, see: D. Badgujar, M. Talwar, S. Asthana, and P. Mahulikar J. Sci. Ind. Res. 66 2007 250
45. H.B. Sun, R.M. Hua, and Y.W. Yin J. Org. Chem. 70 2005 9071
46. B.M. Lynch, C.M. Chen, and Y.-Y. Wigfield Can. J. Chem. 46 1968 1141
47. S. Hartshorn, R. Moodie, and K. Schofield J. Chem. Soc. B 1971 2454
48. F.G. Bordwell, and E.W. Garbisch J. Am. Chem. Soc. 82 1960 3588
49. J.W. Morzycki, A.Z. Wilczewska, and Z. Lotowski Tetrahedron Lett. 37 1996 2079
50. J. Desmurs, M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, and J. Dubac Tetrahedron Lett. 38 1997 8871
51. N.M. Leonard, L.C. Wieland, and R.S. Mohan Tetrahedron 58 2002 8373
52. H. Gaspard-Iloughmane, and C. Le Roux Eur. J. Org. Chem. 2004 2004 2517
53. H. Suzuki, A. Tatsumi, T. Ishibashi, and T. Mori J. Chem. Soc., Perkin Trans. 1 1995 339
54. S. Darvesh, R.S. McDonald, K.V. Darvesh, D. Mataija, S. Mothana, H. Cook, K.M. Carneiro, N. Richard, R. Walsh, and E. Martin Bioorg. Med. Chem. 14 2006 4586
55. Q.-Z. Zhou, and Z.-C. Chen Synth. Commun. 30 2000 3189
56. M.P. Cava, A.A. Deana, K. Muth, and M.J. Mitchell Org. Synth. 41 1961 93
57. C. Tie, J.C. Gallucci, and J.R. Parquette J. Am. Chem. Soc. 128 2006 1162
58. Y.-M. Legrand, M. Gray, G. Cooke, and V.M. Rotello J. Am. Chem. Soc. 125 2003 15789
59. Y. Zhang, S. Patel, and N. Mainolfi Chem. Sci. 3 2012 3196
60. R.A. Bunce, C.L. Smith, and C.L. Knight Org. Prep. Proced. Int. 36 2004 482
61. R. Yamasaki, A. Tanatani, I. Azumaya, S. Saito, K. Yamaguchi, and H. Kagechika Org. Lett. 5 2003 1265
62. J. Shen, T.T. Nguyen, Y.-P. Goh, W. Ye, X. Fu, J. Xu, and C.-H. Tan J. Am. Chem. Soc. 128 2006 13692
63. A. Fischer, D.L. Fyles, G.N. Henderson, and S.R. Mahasay Can. J. Chem. 64 1986 1764
64. J. Rosevear, and J. Wilshire Aust. J. Chem. 38 1985 723
65. R. Reuter, N. Hostettler, M. Neuburger, and H.A. Wegner Eur. J. Org. Chem. 2009 2009 5647
66. B. Schmidt, R. Berger, and F. Hölter Org. Biomol. Chem. 8 2010 1406
67. R.L. Clark, and A.A. Pessolano J. Am. Chem. Soc. 80 1958 1657
68. J.J. Yin, and S.L. Buchwald Org. Lett. 2 2000 1101
69. T. Shepherd, and D.M. Smith J. Chem. Soc., Perkin Trans. 1 1987 501
70. P.E. Verkade, H. Roelfzema, W. Meerburg, and G.S.K. Bosma Recl. Trav. Chim. Pays-Bas Belg. 66 1947 374
71. J.R. Hanson, and H. Saberi J. Chem. Res. 2004 2004 699
72. P. Witjens, B. Wepster, and P. Verkade Recl. Trav. Chim. Pays-Bas 62 1943 523