Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB)

Tetrahedron Letters

Volumn 51, Issue 33, 2010, Pages 4419-4424

  Khan, Abu T ^a   Lal, Mohan ^a   Khan, Md Musawwer ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

1,3 Dicarbonyl compounds; Heterocycles; Multicomponent reactions; Piperidines; TBATB

Indexed keywords

ALCOHOL; ALDEHYDE; AMINE; CARBONYL DERIVATIVE; CRYSTAL SRTUCCRY; PIPERIDINE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CRYSTAL STRUCTURE; DIELS ALDER REACTION; ECONOMIC ASPECT; ONE POT SYNTHESIS; REACTION OPTIMIZATION; ROOM TEMPERATURE;

EID: 77955415647     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.069     Document Type: Article

References (53)

1. J. Zhu, and H. Bienayme Multicomponent Reactions 2005 Wiley Weinheim
2. I. Ugi Pure Appl. Chem. 73 2001 187
3. V. Nair, C. Rajesh, A. Vinod, U.S. Bindu, A.R. Streekenth, J.S. Mathen, and L. Balagopal Acc. Chem. Res. 36 2003 899
4. D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
5. A. Dömling Chem. Rev. 106 2006 17
6. P.A. Tempest Curr. Opin. Drug Disc. 8 2005 776
7. H. Fujioka, K. Murai, O. Kubo, Y. Ohba, and Y. Kita Org. Lett. 9 2007 1687
8. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, and A. Kornienko J. Org. Chem. 72 2007 3443
9. X.S. Wang, Q. Li, J.R. Wu, Y.L. Li, C.S. Yao, and S.J. Tu Synthesis 2008 1902
10. B.M. Trost Angew. Chem., Int. Ed. Engl. 34 1995 259
11. P.A. Wender, S.T. Handy, and D.L. Wright Chem. Ind. 1997 765
12. S. Benetti, R. Romagnoli, C. De Risi, G. Spalluto, and V. Zanirato Chem. Rev. 95 1995 1065
13. P. Langer Chem. Eur. J. 7 2001 3858
14. P. Langer Synthesis 2002 441
15. C. Simon, T. Constantieux, and J. Rodriguez Eur. J. Org. Chem. 2004 4957
16. F. Liéby-Muller, C. Simon, T. Constantieux, and J. Rodriguez QSAR. Comb. Sci. 25 2006 432
17. G.V.M. Sharma, K.L. Reddy, P.S. Lakshmi, and P.R. Krishna Synthesis 2006 55
18. L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z.Y. Fan, H. Tian, and C.T. Qian Tetrahedron 61 2005 1539
19. A.D. Elbein, and R. Molyneux S.W. Pelletier, Alkaloids, Chemical and Biological Perspectives Vol. 57 1987 John Wiley & Sons New York
20. D. O'Hagan Nat. Prod. Rep. 17 2000 435
21. J.W. Daly, T.F. Spande, and H.M. Garraffo J. Nat. Prod. 68 2005 1556
22. P.S. Watson, B. Jiang, and B. Scott Org. Lett. 2 2000 3679
23. S. Petit, J.P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, and J.L. Imbs Eur. J. Med. Chem. 26 1991 19
24. Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, and D. Wall Bioorg. Med. Chem. Lett. 17 2007 1206
25. M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, and R.P. Tripathi Bioorg. Med. Chem. 17 2009 625
26. H. Bin, A.M. Crider, and J.P. Stables Eur. J. Med. Chem. 36 2001 265
27. J. Esquivias, R.G. Arrayas, and J.C. Carretero J. Am. Chem. Soc. 129 2007 1480
28. X.-F. Zhu, J. Lan, and O. Kwon J. Am. Chem. Soc. 125 2003 4716
29. A. Takemiya, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 6042
30. M. Amat, O. Bassas, M.A. Perica's, P. Pasto, and J. Bosch Chem. Commun. 2005 1327
31. R. Martín, C. Murruzzu, M.A. Perics, and A. Riera J. Org. Chem. 70 2005 2325
32. T.P. Lebold, A.B. Leduc, and M.A. Kerr Org. Lett. 11 2009 3770
33. K. Takasu, N. Shindoh, H. Tokuyama, and M. Ihara Tetrahedron 62 2006 11900
34. M. Sales, and A.B. Charette Org. Lett. 7 2005 5773
35. M.S.R. Murty, R. Ram, and J.S. Yadav Tetrahedron Lett. 49 2008 1141
36. R.M. Carballo, M.A. Ramirez, M.L. Rodriguez, V.S. Martin, and J.I. Padron Org. Lett. 8 2006 3837
37. A.P. Dobbs, and S.J.J. Guesne Synlett 2005 2101
38. S. Fustero, D. Jimenez, J. Moscardo, S. Catalan, and C. del Pozo Org. Lett. 9 2007 5283
39. F.A. Davis, B. Chao, and A. Rao Org. Lett. 3 2001 3169
40. A.T. Khan, T. Parvin, and L.H. Choudhury J. Org. Chem. 73 2008 8398
41. P.A. Clarke, A.V. Saytsev, and A.C. Whitwood Tetrahedron Lett. 48 2007 5209
42. M.K. Chaudhuri, A.T. Khan, B.K. Patel, D. Dey, W. Kharmawophlang, T.R. Lakshmipravha, and G.C. Mandal Tetrahedron Lett. 39 1998 8163
43. E. Mondal, G. Bose, and A.T. Khan Synlett 2001 785
44. E. Mondal, P.R. Sahu, G. Bose, and A.T. Khan Tetrahedron Lett. 43 2002 2843
45. G. Bose, P.M.B. Barua, M.K. Chaudhuri, D. Kalita, and A.T. Khan Chem. Lett. 2001 290
46. G. Bose, E. Mondal, A.T. Khan, and M.J. Bordoloi Tetrahedron Lett. 42 2001 8907
47. Xu.F. Lin, S.L. Cui, and Y.G. Wang Synth. Commun. 36 2006 3153
48. V. Kavala, and B.K. Patel Eur. J. Org. Chem. 2 2005 441
49. R. Gopinath, S.J. Haque, and B.K. Patel J. Org. Chem. 67 2002 5842
50. R. Gopinath, and B.K. Patel Org. Lett. 2 2000 4177
51. S. Naik, R. Gopinath, and B.K. Patel Tetrahedron Lett. 42 2001 7679
52. 2 (571.54): C, 71.45; H, 5.64; N, 4.90. Found: C, 71.34; H, 5.53; N, 5.02.
53. Complete crystallographic data of 1l for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 775694. Copies of this information may be obtained free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 1223 336033, e-mail: deposit@ccdc.cam.ac.uk or via: www.ccdc.cam.ac.uk ).