A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by FeCl3·6H2O in presence of hydroxylamine hydrochloride

Tetrahedron Letters

Volumn 56, Issue 14, 2015, Pages 1915-1918

  Mahajan, Sheena ^a   Sharma, Bhavana ^a   Kapoor, Kamal K ^a  

^a UNIVERSITY OF JAMMU   (India)

Author keywords

Amides; Beckmann rearrangement; Eco friendly; Ferric chloride; Solid phase; Solvent free reaction

Indexed keywords

1,2 DICHLOROETHANE; AMIDE; BENZALDEHYDE; BENZONITRILE; BENZOPHENONE; CARBON; FERRIC CHLORIDE; HYDROXYLAMINE; ISATIN; KETONE; LEWIS ACID; NINHYDRIN; OXIME; SOLVENT;

ARTICLE; BECKMANN REARRANGEMENT; CATALYSIS; CATALYST; CHEMICAL BOND; HEATING; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID; TAUTOMERIZATION; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 84925464980     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.02.110     Document Type: Article

References (77)

1. E. Beckmann Berichte der Deutschen Chemischen Gesellschaft 19 1886 988 993
2. A.H. Blatt Chem. Rev. 12 1933 215 260
3. L.G. Donaruma, and W.Z. Heldt Org. React. 11 1960 1 156
4. M.T. Nguyen, G. Raspoet, and L.G. Vanquickenborne J. Am. Chem. Soc. 119 1997 2552 2562
5. R.E. Gawly Org. React. 35 1988 14 24
6. U. Nubbemeyer Top. Curr. Chem. 216 2001 125 196
7. Y. Izumi, S. Sato, and K. Urabe Chem. Lett. 1983 1649
8. M.B. Smith, and J. March Advanced Organic Chemistry Vol. 9 2001 John Wiley & Sons New York 1415 1416
9. For selected examples in vapor phase, see: (a) Y. Ko, M.H. Kim, S.J. Kim, G. Seo, M.-Y. Kim, and Y.S. Uh Chem. Commun. 2000 829 830
10. K.V.V.S.B.S.R. Murthy, M. Chandrakala, S.J. Kulkarni, and K.V. Raghavan Ind. J. Chem. Tech. 8 2001 368 370
11. D. Mao, Q. Chen, and G. Lu Appl. Catal. A: Gen. 244 2 2003 273 282
12. Y. Izumi, H. Ichihashi, Y. Shimazu, M. Kitamura, and H. Sato Bull. Chem. Soc. Jpn. 80 7 2007 1280 1287
13. V.R.R. Marthala, S. Rabl, J. Huang, S.A.S. Rezai, B. Thomas, and M. Hunger J. Catal. 257 2008 134 141
14. S. Nagashima, S. Kamiguchi, S. Ohguchi, and T. Chihara Catal. Today 164 2011 135 138
15. T. Ushikubo, and K. Wada J. Catal. 148 1994 138
16. L.X. Dai, K. Koyama, M. Miyamoto, and T. Tatsumi Appl. Catal. A: Gen. 189 1999 237
17. For selected examples in liquid phase mediated by small organic molecules, see: (a) M. Zhu, C. Cha, W.-P. Deng, and X.-X. Shi Tetrahedron Lett. 47 2006 4861 4863
18. M. Hashimoto, Y. Obora, S. Sakaguchi, and Y. Ishii J. Org. Chem. 73 2008 2894 2897
19. H.-J. Pi, J.-D. Dong, N. An, W. Du, and W.-P. Deng Tetrahedron 65 2009 7790 7793
20. V.P. Srivastava, R. Patel Garima, L. Dhar, and S. Yadav Chem. Commun. 2010 5808 5810
21. L.D.S. Yadav, R. Patel, and V.P. Srivastava Synthesis 11 2010 1771 1776
22. J.K. Augustine, R. Kumar, A. Bombrun, and A.B. Mandal Tetrahedron Lett. 52 2011 1074 1077
23. F. Xu, N.-G. Wang, Y.-P. Tian, Y.-M. Chen, and W.-C. Liu Synth. Commun. 42 2012 3532 3539
24. L. De Luca, G. Giacomelli, and A. Porcheddu J. Org. Chem. 67 2002 6272 6274
25. S. Chandrasekhar, and K. Gopalaiah Tetrahedron Lett. 44 2003 755 756
26. For selected examples using metallic Lewis acids, see: (a) M. Arisawa, and M. Yamaguchi Org. Lett. 3 2001 311
27. J.S. Yadav, B.V.S. Reddy, A.V. Madhavi, and Y.S.S. Ganesha J. Chem. Res., Synop. 2002 236
28. S.K. De Synth. Commun. 34 2004 3431
29. C. Ramalingan, and Y.T. Park J. Org. Chem. 72 2007 4536 4538
30. A.J. Thakur, A. Boruah, D. Prajapati, and J.S. Sandhu Synth. Commun. 30 2000 2105
31. S.K. Sharma, S.D. Bishopp, C.L. Allen, R. Lawrence, M.J. Bamford, A.A. Lapkin, P. Plucinski, R.J. Watson, and J.M.J. Williams Tetrahedron Lett. 52 2011 4252 4255
32. A. Martinez-Asencio, M. Yus, and D.J. Ramon Tetrahedron Lett. 68 2012 3948 3951
33. C.L. Allen, C. Burel, and J.M.J. Williams Tetrahedron Lett. 51 2010 2724 2726
34. Y. Izumi Chem. Lett. 1990 2171
35. H. Sato, H. Yoshioka, and Y. Izumi J. Mol. Catal. A: Chem. 149 1999 25
36. For selected examples in supercritical water, see: (a) O. Sato, Y. Ikushima, and T. Yokoyama J. Org. Chem. 63 1998 9100 9102
37. Y. Ikushima, K. Hatakeda, O. Sato, T. Yokoyama, and M. Arai Angew. Chem., Int. Ed. 38 1999 2910 2914
38. Y. Ikushima, K. Hatakeda, O. Sato, T. Yokoyama, and M. Arai J. Am. Chem. Soc. 122 2000 1908 1918
39. M. Boero, T. Ikeshoji, C.C. Liew, K. Terakura, and M. Parrinello J. Am. Chem. Soc. 126 2004 6280 6286
40. For selected examples in ionic liquids, see: (a) J.K. Lee, D. Kim, C.E. Song, and S. Lee Synth. Commun. 33 2003 2301
41. K. Qiao, Y. Deng, C. Yokoyama, H. Sato, and M. Yamashina Chem. Lett. 33 2004 1350 1351
42. J. Gui, Y. Deng, Z. Hu, and Z. Sun Tetrahedron Lett. 45 2004 2681 2683
43. S.P. Verevkin, V.N. Emel'yanenko, A.V. Toktonov, P. Goodrich, and C. Hardacre Ind. Eng. Chem. Res. 48 2009 9809 9816
44. T. Blasco, A. Corma, S. Iborra, I. Lezcano-Gonzalez, and R. Monton J. Catal. 275 2010 78 83
45. K. Sugamoto, Y. Matsushita, and T. Matsui Synth. Commun. 41 2011 879 884
46. For selected examples in solid phase systems, see: (a) A.I. Bosch, P. De la Cruz, E. Diez-Barra, A. Loupy, and F. Langa Synlett 1995 1259
47. M. Ghiaci, and H. Imanzadeh Synth. Commun. 28 1998 2275
48. B. Touaux, F. Texier-Boullet, and J. Hamelin Heteroatom. Chem. 9 1998 351
49. B.M. Khadilkar, and D.J. Upadhyaya Synth. Commun. 2002 1867 32
50. F.M. Moghaddam, A.A.R. Rad, and H. Zali-Boinee Synth. Commun. 34 2004 2071 2075
51. Zheng Li, and Zhong Lu Lett. Org. Chem. 5 2008 495 501
52. K.S. Niralwad, B.B. Shingate, and M.S. Shingare Lett. Org. Chem. 8 4 2011 274 277
53. I. Ganboa, and C. Palomo Synth. Commun. 13 1983 941
54. H. Sharghi, and M. Hosseini Synthesis 8 2002 1057 1060
55. M.H. Sarvari, and H. Sharghi J. Chem. Res., Synop. 3 2003 176 178
56. H. Eshghi, and Z. Gordi Synth. Commun. 33 2003 2971
57. S. Chandrasekhar, and K. Gopalaiah Tetrahedron Lett. 44 2003 7437 7439
58. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, and J. Thanusu Lett. Org. Chem. 2 2005 444
59. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, and R. Govindaraju ARKIVOC 13 2006 130 141
60. M.H. Sarvari, and H. Sharghi J. Chem. Res. 3 2006 205 208
61. H. Eshghi, and A. Hassankhani J. Korean Chem. Soc. 51 2007 361 364
62. S. Sadaphal J. Korean Chem. Soc. 52 2008 454 456
63. S. Kumar Pallvi, S. Chadha, S. Dham, T. Hundal, and K.K. Kapoor Tetrahedron Lett. 2012 1905 53
64. S. Chadha, R. Khajuria, S. Paul, and K.K. Kapoor Indian J. Chem. 52B 2013 259
65. R. Khajuria, Y. Saini, and K.K. Kapoor Tetrahedron Lett. 54 2013 5699
66. R. Khajuria Ambica, Y. Saini, and K.K. Kapoor Indian J. Chem. 53B 2014 1122
67. R. Khajuria, and K.K. Kapoor Curr. Microwave Chem. 2 2014 110
68. R.K. Sharma, R. Khajuria, and K.K. Kapoor Synth. Commun. 44 2014 3538
69. M.M. Khodaei, F.A. Meybodi, N. Rezai, and P. Salehi Synth. Commun. 31 2001 2047 2050
70. S.R. Narahari, B.R. Reguri, and K. Mukkanti Tetrahedron Lett. 52 2011 4888
71. K. Banerjee, and A.K. Mitra Ind. J. Chem. 44B 2005 1876 1879
72. M. Karthikeyan, R.C. Glen, and A. Bender J. Chem. Inf. Model. 45 2005 581 590
73. S. Budavari, M.J. O' Neil, A. Smith, P.E. Heckelman, and J.F. Kinneary The Merck Index 1996 Merck and Co. Inc. Whitehouse Station, N.J. U.S.A. 6679
74. G.L. Grunewald, and V.H.J. Dahanukar Heterocycl. Chem. 31 1994 1609
75. 4th ed. Dictionary of Organic Compounds 1965 E&FN Spain, London
76. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, and A.R. Tatchell Vogel's Textbook of Practical Organic Chemistry 5th ed. 1989 Longman Harlow
77. J.S. Yadav, B.V.S. Reddy, K. Premalatha, and K.S. Shankar Synthesis 23 2008 3787 3792