Green progression for synthesis of regioselective β-amino alcohols and chemoselective alkylated indoles

Organic Process Research and Development

Volumn 14, Issue 6, 2010, Pages 1457-1463

  Thirupathi, Boningari ^a   Srinivas, Rapelli ^a   Prasad, Avvari N ^a   Kumar, J K Prashanth ^a   Reddy, Benjaram M ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; C-C BONDS; CHEMOSELECTIVE; ENVIRONMENTALLY BENIGN; FRIEDEL-CRAFTS ALKYLATION; MIXED OXIDE CATALYSTS; ORGANIC SYNTHESIS; REGIO-SELECTIVE; SOLID ACID CATALYSTS; TIO; ZIRCONIA MATERIALS;

ALCOHOLS; AMINES; CATALYSTS; ZIRCONIA;

REGIOSELECTIVITY;

EID: 78649646810     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op1002177     Document Type: Article

References (60)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
2. Eissen, M.; Metzger, J. O.; Schmidt, E.; Schneidewind, V. Angew. Chem., Int. Ed. 2002, 41, 414
3. Special Topic Issue on Green Chemistry: Acc. Chem. Res. 2002, 35, 685.
4. Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: Chichester, UK, 1997.
5. Organic Synthesis in Water: Grieco, P. A., Ed.; Blake Academic and Professional: London, 1998.
6. Tok, J. B.-H.; Rando, R. R. J. Am. Chem. Soc. 1998, 120, 8279
7. Ke, X.; Hu, H.; Zhang, K.; Xu, W.; Zhu, Q.; Wu, L.; Hu, X. Chem. Commun. 2009, 1037
8. Hewett, C. L.; Savage, D. S.; Lewis, J. J.; Sugrue, M. F. J. Pharm. Pharmacol. 1964, 16, 765
9. Daniell, C. J.; Cross, M.; Sneyd, J. R.; Thompson, P.; Andrews, C. J. Br. J. Anaesth. 1996, 76, 586
10. Hill-Venning, C.; Peters, J. A.; Callachan, H. Neuropharmacology 1996, 35, 1209
11. Anderson, A.; Boyd, A. C.; Byford, A.; Gemmell, D. K. J. Med. Chem. 1997, 40, 1668
12. He, Q.; Jiang, D. Leuk. Res. 1999, 23, 369
13. He, Q.; Na, X. Leuk. Res. 2001, 25, 455
14. Roy, J.; Deroy, P.; Poirier, D. J. Comb. Chem. 2007, 9, 347
15. Liao, Y. F.; Wang, B.-J.; Hsu, W. M.; Lee, H.; Liao, C. Y.; Wu, S. Y.; Cheng, H. T.; Hu, M. K. Mol. Pharmacol. 2007, 71, 588
16. Bakshi, P.; Wolfe, M. S. J. Med. Chem. 2004, 47, 6485
17. Beaulieu, P. L.; Wernic, D.; Abraham, A.; Anderson, P. C.; Bogri, T.; Bousquet, Y.; Croteau, G.; Guse, I.; Lamarre, D.; Liard, F.; Paris, W.; Thibeault, D. J. Med. Chem. 1997, 40, 2164
18. Kempf, D. J.; Codavoci, L.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.; Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, D. W. J. Med. Chem. 1993, 36, 320
19. Medou, M.; Priem, G.; Rocheblave, L.; Pepe, G.; Meyer, M.; Chermann, J. C.; Kraus, J. L. Eur. J. Med. Chem. 1999, 34, 625
20. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735
21. Kick, E. K.; Roe, D. C.; Skillman, A. G.; Liu, G.; Ewing, T. J. A.; Sun, Y.; Kuntz, I. D.; Ellman, J. A. Chem. Biol. 1997, 4, 297
22. Haque, T. S.; Skillman, A. G.; Lee, C. E.; Habashita, H.; Gluzman, I. Y.; Ewing, T. J. A.; Goldberg, D. E.; Kuntz, I. D.; Ellman, J. A. J. Med. Chem. 1999, 42, 1428
23. Santos, M. D.; Crousse, B.; Bonnet-Delpon, D. Tetrahedron Lett. 2009, 50, 857
24. Maillard, M. C.; Hom, R. K.; Benson, T. E.; Moon, J. B.; Mamo, S.; Bienkowski, M.; Tomasselli, A. G.; Woods, D. D.; Prince, D. B.; Paddock, D. J.; Emmons, T. L.; Tucker, J. A.; Dappen, M. S.; Brogley, L.; Thorsett, E. D.; Jewett, N.; Sinha, S.; John, V. J. Med. Chem. 2007, 50, 776
25. Tewari, N.; Tiwari, V. K.; Tripathi, R. P.; Chaturvedi, V.; Srivastava, A.; Srivastava, R.; Shukla, P. K.; Chaturvedi, A. K.; Gaikwad, A.; Sinha, S.; Srivastava, B. S. Bioorg. Med. Chem. Lett. 2004, 14, 329
26. Press, J. B.; Falotico, R.; Hajos, Z. G.; Sawyers, R. A.; Kanojia, R. M.; Williams, L.; Haertlein, B.; Kauffman, J. A.; Lakas-Weiss, C.; Salata, J. J. J. Med. Chem. 1992, 35, 4509
27. Barton, D. L.; Press, J. B.; Hajos, Z. G.; Sawyers, R. A. Tetrahedron: Asymmetry 1992, 3, 1189
28. Butrous, G. S.; Debbas, N. M. G.; Erwin, J.; Davies, D. W.; Keller, H. P.; Lunnon, M. W.; Nathan, A. W.; Camm, A. J. Eur. Heart J. 1988, 9, 489
29. Sircar, I.; Haleen, S. J.; Burke, S. E. J. Med. Chem. 1992, 35, 4442
30. Suzuki, T.; Fukazawa, N.; San-nohe, K. J. Med. Chem. 1997, 40, 2047
31. Taguchi, A.; Schuth, F. Microporous Mesoporous Mater. 2005, 77, 1
32. Rao, K. N.; Reddy, B. M.; Abhishek, B.; Seo, Y.-H.; Jiang, N.; Park, S.-E. Appl. Catal., B 2009, 91, 649
33. Reddy, B. M.; Lee, S.-C.; Han, D.-S.; Park, S.-E. Appl. Catal., B 2009, 87, 230
34. Azoulay, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2005, 7, 4593
35. Fung, J.; Wang, I. J. Catal. 1991, 130, 577
36. Reddy, B. M.; Manohar, B.; Mehdi, S. J. Solid State Chem. 1992, 97, 233
37. Reddy, B. M.; Chowdhury, B.; Smirniotis, P. G. Appl. Catal., A 2001, 211, 19
38. Mullins, W. M.; Averbach, B. Surf. Sci. 1988, 206, 29
39. Newnham, R. E. J. Am. Ceram. Soc. 1967, 50, 216
40. Park, Y. Mater. Res. Bull. 1998, 33, 1325
41. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275
42. Klijn, J. E.; Engberts, J. B. N. Nature 2005, 435, 746
43. Pirrung, M. C. Chem.- Eur. J. 2006, 12, 1312
44. Recently, we introduced zeo-click-MCR concept for organic cascade syntheses by using zeolites in water
45. Thirupathi, B.; Olmos, A.; Reddy, B. M.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2010, DOI: 10.1002/ejoc.200.
46. Chassaing, S.; Alix, A.; Thirupathi, B.; Karim, S. S. S.; Keller, M.; Kuhn, P.; Louis, B.; Sommer, J.; Pale, P. Synthesis 2010, 1557
47. Béneteau, V.; Olmos, A.; Thirupathi, B.; Sommer, J.; Pale, P. Tetrahedron Lett. 2010, 51, 3673
48. For recent reviews on solid acid activity under green conditions
49. Reddy, B. M.; Patil, M. K. Chem. Rev. 2009, 109, 2185
50. Reddy, B. M.; Patil, M. K. Curr.Org. Chem. 2008, 12, 118
51. Arata, K. Green Chem. 2009, 11, 1719
52. Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287
53. Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem. 1991, 56, 5939
54. Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.; Sadayori, N.; Wilson, J. G.; Nakamura, H. J. Chem. Soc., Chem. Commun. 1993, 1201
55. Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597
56. Mojtahedi, M. M.; Saidi, M. R.; Bolourtchian, M. J. Chem. Res. (S) 1999, 22, 128
57. Kotsuki, H.; Teraguchi, M.; Shimomoto, N.; Ochi, M. Tetrahedron Lett. 1996, 37, 3727
58. Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 5386
59. Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Synlett 2002, 1550
60. Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2007, 48, 173