InCl3-catalyzed four-component reaction: A novel synthesis of N-carbazolyl dihydropyridines

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6805-6808

  Yamuna, Ezhumalai ^a   Zeller, Matthias ^b   Rajendra Prasad, Karnam Jayarampillai ^a  

^a BHARATHIAR UNIVERSITY   (India)

^b YOUNGSTOWN STATE UNIVERSITY   (United States)

Author keywords

1,4 Dipolar addition; Four component reaction; InCl3; N Carbazolyldihydropyridines

Indexed keywords

ALDEHYDE; CARBAZOLE DERIVATIVE; DIHYDROPYRIDINE; ESTER; INDIUM CHLORIDE; MALONONITRILE; N CARBAZOLYLDIHYDROPYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; MICROWAVE COOKING; REACTION TIME; SYNTHESIS;

EID: 80755175766     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.044     Document Type: Article

References (66)

1. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123
2. N.K. Terret, M. Gardner, D.W. Gordon, R.J. Kobylecki, and J. Steel Tetrahedron 51 1995 8135
3. A. Domling Chem. Rev. 106 2006 17
4. C. Safak, and R. Simsek Mini Rev. Med. Chem. 6 2006 747
5. M. Katoh, M. Nakajima, N. Shimada, H. Yamazaki, and T. Yokoi Eur. J. Clin. Pharmacol. 55 2000 843
6. P. Ruggenenti, A. Perna, R. Benini, and G. Remuzzi J. Am. Soc. Nephrol. 9 1998 2096
7. H. Glossmann, D.R. Ferry, A. Goll, J. Striessnig, and G. Zernig Arzneimittelforschung 35 1985 1917
8. W.C. Matowe, M. Akula, E.E. Knaus, and M.W. Wolowyk Proc. West. Pharmacol. Soc. 32 1989 305
9. D. Vo, W.C. Matowe, M. Ramesh, N. Iqbal, M.W. Wolowyk, S.E. Howlett, and E.E. Knaus J. Med. Chem. 38 1995 2851
10. D. Vo, J.T. Nguyen, C.-A. McEwen, R. Shan, and E.E. Knaus Drug Dev. Res. 56 2002 1
11. N. Edraki, A.R. Mehdipour, M. Khoshneviszadeh, and R. Miri Drug Discovery Today 14 2009 1058
12. H.P. Husson A. Brossi, The Alkaloids Chemistry and Pharmacology 1985 Academic Press Orlando 1 Vol. 26
13. D.P. Chakraborty G.A. Cordell, The Alkaloids 1993 Academic New York, NY 257 Vol. 44
14. H.J. Knölker C.J. Moody, Advances in Nitrogen Heterocycles 1995 JAI Greenwich 173 Vol. 1
15. S. Omura, Y. Sasaki, Y. Iwai, and H. Takeshima J. Antibiot. 48 1995 535
16. P.T. Gallagher Science of Synthesis Vol. 10 2000 Thieme Stuttgart 693
17. M. Laronze, M. Boisbrun, S. Leonce, B. Pfeiffer, P. Renard, O. Lozach, L. Meijer, A. Lansiaux, C. Bailly, J. Sapi, and J.Y. Laronze Bioorg. Med. Chem. 13 2005 2263
18. A.R. Howard-Jones, and C.T. Walsh J. Am. Chem. Soc. 128 2006 12289
19. H.-J. Knölker, and K.R. Reddy G.A. Cordell, The Alkaloids: Chemistry and Biology 2008 Academic Press, Elsevier London 1 Vol. 65
20. T.A. Choi, R. Czerwonka, R. Forke, A. Jagar, J. Knöll, M.P. Krähl, T. Krause, K.R. Reddy, S.G. Franzblau, and H.-J. Knölker Med. Chem. Res. 17 2008 374
21. H.-J. Knölker, and K.R. Reddy Chem. Rev. 102 2002 4303
22. I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127
23. C.J. Moody Synlett 1994 681
24. J. Bergman, and B. Pelcman Pure Appl. Chem. 62 1990 1967
25. R. Huisgen R. Castle, Topics in Heterocyclic Chemistry 1969 John Wiley and Sons New York, NY 223 Chapter 8
26. R.Z. Huisgen Chem. 8 1968 290
27. R. Huisgen, M. Morikawa, K. Herbig, and E. Brunn Chem. Ber. 100 1967 1094
28. R.M. Acheson, and A.O. Plunkett J. Chem. Soc. 1964 2676
29. R.M. Acheson, and J. Woollard J. Chem. Soc., Perkin Trans. 1 1975 438
30. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and L. Balagopal Acc. Chem. Res. 36 2003 899
31. V. Nair, R.S. Menon, A. Sreekanth, N. Abhilash, and A.T. Biju Acc. Chem.Res. 39 2006 520
32. V. Nair, S. Devipriya, and E. Suresh Tetrahedron 64 2008 3567
33. V. Nair, S. Devipriya, and E. Suresh Tetrahedron Lett. 48 2007 3667
34. V. Nair, A. Deepth, P.B. Beneesh, and S. Eringathodi Synthesis 2006 1443
35. I. Yavari, A. Mirzaei, L. Moradi, and G. Khalili Tetrahedron Lett. 51 2010 396
36. I. Yavari, S. Seyfi, and Z. Hossaini Tetrahedron Lett. 51 2010 2193
37. I. Yavari, M. Piltan, and L. Moradi Tetrahedron 65 2009 2067
38. I. Yavari, A. Mokhtarporyani-Sanandaj, L. Moradi, and A. Mirzaei Tetrahedron 64 2008 5221
39. K. Harju, J. Vesterinen, and J. Yli-Kauhaluoma Org. Lett. 11 2009 2219
40. Y. Shibata, K. Noguchi, M. Hirano, and K. Tanaka Org. Lett. 10 2008 2825
41. C. Ma, H.F. Ding, and Y.G. Wang Org. Lett. 8 2006 3133
42. C. Ma, and Y.W. Yang Org. Lett. 7 2005 1343
43. E.Y. Xia, J. Sun, R. Yao, and C.G. Yan Tetrahedron 66 2010 3569
44. M. Bayat, H. Imanieh, and F. Hassanzadeh Tetrahedron Lett. 51 2010 1873
45. M.B. Teimouri, T. Abbasi, S. Ahmadian, M. Heravi, and R. Bazhrang Tetrahedron 65 2009 8120
46. J.S. Yadav, B.V.S. Reddy, N.N. Yadav, M.K. Gupta, and B. Sridhar J. Org. Chem. 73 2008 6857
47. H. Cavdar, and N. Saraoglu J. Org. Chem. 71 2006 7793
48. A. Srikrishna, M. Sridharan, and K.R. Prasad Tetrahedron Lett. 51 2010 3651
49. M.B. Teimouri, and T. Abbasi Tetrahedron 66 2010 3795
50. J. Bezensek, T. Kolesa, U. Groselj, J. Wagger, K. Stare, A. Meden, J. Svete, and B. Stanovnik Tetrahedron Lett. 51 2010 3392
51. P. Singh, P. Sharma, K. Bisetty, and M. Mahajan Tetrahedron 65 2009 8478
52. A. Alizadeh, S. Rostamnia, and N. Hosseinpour Tetrahedron Lett. 50 2009 1533
53. T.B. Nguyen, A. Martel, R. Dhal, and G. Dujardin Org. Lett. 10 2008 4493
54. W.B. Liu, H.F. Jiang, and L.B. Huang Org. Lett. 12 2010 312
55. Y.X. Shen, H.F. Jiang, and Z.W. Chen J. Org. Chem. 75 2010 1321
56. W.B. Liu, H.F. Jiang, S.F. Zhu, and W. Wang Tetrahedron 65 2009 7985
57. W.B. Liu, H.F. Jiang, and C.L. Qiao Tetrahedron 65 2009 2110
58. H. Cao, X.J. Wang, and H.F. Jiang Chem. -Eur. J. 14 2008 11623
59. C.J. Li, and T.H. Chan Tetrahedron 55 1999 11149
60. G. Babu, and P.T. Perumal Aldrichim. Acta 33 2000 16
61. R. Ghosh Indian J. Chem. 40B 2001 550
62. J.S. Yadav, A. Antony, J. George, and B.V. Subba Reddy Curr. Org. Chem. 14 2010 414
63. B.V. Subba Reddy, M. Ramana Reddy, G. Narasimhulu, and J.S. Yadav Tetrahedron Lett. 51 2010 5677
64. I.R. Siddiqui, S. Shamim, A. Singh, V. Srivastava, and S. Yadav Arkivoc 2010 232
65. G. Shanthi, and P.T. Perumal Tetrahedron Lett. 50 2009 3959
66. 3: C, 72.79; H, 5.48; N, 11.71 Found: C, 72.74; H, 5.42; N, 11.75.