Nano indium oxide catalyzed efficient synthesis of propargylamines via C-H and C-Cl bond activations

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4437-4439

  Rahman, Matiur ^a   Bagdi, Avik Kr ^a   Majee, Adinath ^a   Hajra, Alakananda ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

C H and C Cl bond activations; Coupling; Nano indium oxide; Propargylamines; Recycling

Indexed keywords

AMINE; DICHLOROMETHANE; INDIUM; METAL OXIDE; NANO INDIUM OXIDE; PROPARGYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ENZYME ACTIVITY; SYNTHESIS;

EID: 79960840428     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.067     Document Type: Article

References (66)

1. G. Dyker Handbook of C-H Transformations 2005 Wiley-VCH Weinheim
2. G. Dyker Angew. Chem., Int. Ed. 38 1999 1698
3. Y. Zhang, P. Li, M. Wang, and L. Wang J. Org. Chem. 74 2009 4364
4. J.S. Yadav, B.V.S. Reddy, A.V. Gopal, and K.S. Patil Tetrahedron Lett. 50 2009 3493
5. X. Zhang, and A. Corma Angew. Chem., Int. Ed. 47 2008 4358
6. P. Li, and L. Wang Tetrahedron 63 2007 5455
7. M. Wang, P. Li, and L. Wang Eur. J. Org. Chem. 2008 2255
8. B.M. Choudary, C. Sridhar, M.L. Kantam, and B. Sreedhar Tetrahedron Lett. 45 2004 7319
9. M.L. Kantam, B.V. Prakash, C.R.V. Reddy, and B. Sreedhar Synlett 2005 2329
10. K.M. Reddy, N.S. Babu, P.S.S. Prasad, and N. Lingaiah Tetrahedron Lett. 47 2006 7563
11. S.B. Park, and H. Alper Chem. Commun. 10 2005 1315
12. N. Gommermann, C. Koradin, K. Polborn, and P. Knochel Angew. Chem., Int. Ed. 42 2003 5763
13. T.F. Knopfel, P.A. Aschwanden, T. Ichikawa, T. Watanabe, and E.M. Carreira Angew. Chem., Int. Ed. 43 2004 5971
14. K.A. Bisai, and V.K. Singh Org. Lett. 8 2006 2405
15. C.J. Li, and C. Wei Chem. Commun. 2002 268
16. C. Wei, and C.-J. Li J. Am. Chem. Soc. 125 2003 9584
17. C. Wei, Z. Li, and C.-J. Li Org. Lett. 5 2003 4473
18. C. Wei, and C.-J. Li J. Am. Chem. Soc. 124 2002 5638
19. C. Wei, J.T. Mague, and C.-J. Li Proc. Natl. Acad. Sci. U.S.A. 101 2004 5749
20. Q. Zhang, J.-X. Chen, W.-X. Gao, J.-C. Ding, and H.-Y. Wu Appl. Organomet. Chem. 24 2010 809
21. K. Namitharan, and K. Pitchumani Eur. J. Org. Chem. 2010 411
22. T. Napta, H. Takaya, and S.I. Murahashi Chem. Rev. 98 1998 2599
23. Y. Yamamoto, H. Hayashi, T. Saigoku, and T.H. Nishiyama J. Am. Chem. Soc. 127 2005 10804
24. B. Jiang, and M. Xu Angew. Chem., Int. Ed. 43 2004 2543
25. M.A. Huffman, N. Yasuda, A.E. DeCamp, and E.J.J. Grabowski J. Org. Chem. 60 1995 1590
26. M. Konishi, H. Ohkuma, T. Tsuno, T. Oki, G.D. VanDuyne, and J. Clardy J. Am. Chem. Soc. 112 1990 3715
27. M. Miura, M. Enna, K. Okuro, and M. Nomura J. Org. Chem. 60 1995 4999
28. A. Jenmalm, W. Berts, Y.L. Li, K. Luthman, I. Csoregh, and U. Hacksell J. Org. Chem. 59 1994 1139
29. D. Aguilar, M. Contel, and E.P. Urriolabeitia Chem. Eur. J. 16 2010 9287
30. D. Yu, and Y. Zhang Adv. Synth. Catal. 353 2011 163
31. D. Astruc, F. Lu, and J.R. Aranzaes Angew. Chem., Int. Ed. 44 2005 7852
32. D. Astruc Inorg. Chem. 46 2007 1884
33. J. Durand, E. Teuma, and M. Gomez Eur. J. Inorg. Chem. 2008 3577
34. V. Polshettiwar, B. Baruwati, and R.S. Varma Green Chem. 11 2009 127
35. L. Adak, K. Chattopadhyay, and B.C. Ranu J. Org. Chem. 74 2009 3982
36. R. Dey, K. Chattopadhyay, and B.C. Ranu J. Org. Chem. 73 2008 9461
37. M. Moreno-Manas, and R. Pleixats Acc. Chem. Res. 36 2003 638
38. S. Jammi, S. Sakthivel, T. Rout, S. Mandal, R. Mitra, P. Saha, and T. Punniyamurthy J. Org. Chem. 74 2009 1971
39. W. Zhang, X. Zhang, Y. Tian, Y. Yue, Y. Guo, and Z. Wang J. Org. Chem. 76 2011 4741
40. R. Ghosh, and S. Maiti J. Mol. Catal. A: Chem. 264 2007 1
41. T.P. Loh, and G.L. Chua Chem. Commun. 2006 2739
42. K.K. Chauhan, and C.G. Frost J. Chem. Soc., Perkin Trans. 1 2000 3015
43. P. Cintas Synlett 1995 1087
44. J. Podlech, and T.C. Maier Synthesis 2003 633
45. V. Nair, S. Ros, C.N. Jayan, and B.S. Pillai Tetrahedron 60 2004 1959
46. B.C. Ranu Eur. J. Org. Chem. 2000 2347
47. J. Auge, N. Lubin-Germain, and J. Uziel Synthesis 2007 1739
48. H.A.F. Hoppe, G.C. Lloyd-Jones, M. Murray, T.M. Peakman, and K.E. Walsh Angew. Chem., Int. Ed. 37 1998 1545
49. B.M. Trost, and R.C. Livingston J. Am. Chem. Soc. 130 2008 11970
50. Y. Nishimoto, H. Ueda, Y. Inamoto, M. Yasuda, and A. Baba Org. Lett. 12 2010 3390
51. M. Yasuda, S. Yamasaki, Y. Onishi, and A. Baba J. Am. Chem. Soc. 126 2004 7186
52. K. Koszinowski J. Am. Chem. Soc. 132 2010 6032
53. J.S. Yadav, A. Antony, J. George, and B.V.S. Reddy Eur. J. Org. Chem. 2010 591
54. J.S. Jadav, A. Antony, J. George, and B.V.S. Reddy Curr. Org. Chem. 14 2010 414
55. D. Kundu, M. Samim, A. Majee, and A. Hajra Chem. Asian J. 6 2011 406
56. D. Kundu, A. Majee, and A. Hajra Tetrahedron Lett. 50 2009 2668
57. S. Urinda, D. Kundu, A. Majee, and A. Hajra Heteroat. Chem. 20 2009 232
58. B.C. Ranu, S.S. Dey, and A. Hajra Tetrahedron 58 2002 2529
59. B.C. Ranu, S. Samanta, and A. Hajra Synlett 2002 987
60. B.C. Ranu, and A. Hajra J. Chem. Soc., Perkin Trans. 1 2001 355
61. B.C. Ranu, and A. Hajra J. Chem. Soc., Perkin Trans. 1 2001 2262
62. B.C. Ranu, A. Hajra, and U. Jana Tetrahedron Lett. 41 2002 531
63. B.C. Ranu, A. Hajra, and U. Jana J. Org. Chem. 65 2000 6270
64. B.C. Ranu, A. Hajra, and U. Jana Org. Lett. 1 1999 1141
65. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Org. Lett. 11 2009 1697
66. 29N: C, 80.65; H, 13.08; N, 6.27. Found: C, 80.49; H, 12.95; N, 6.12.