Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4- dihydropyridine derivatives via Hantzsch reaction

Tetrahedron Letters

Volumn 46, Issue 34, 2005, Pages 5771-5774

  Ko, Shengkai ^a   Sastry, M N V ^a   Lin, Chunchi ^a   Yao, Ching Fa ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

Catalytic amounts; Hantzsch reaction; Molecular iodine; Simple and efficient; Synthesis of 1,4 dihydropyridine

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; IODINE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 22544457892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.148     Document Type: Article

References (67)

1. D. Mauzeral, and F.H. Westheimer J. Am. Chem. Soc. 77 1955 2261
2. P.G. Baraldi, A. Chiarini, R. Budriesi, M. Roberti, A. Casolar, S. Manfredini, D. Simoni, V. Zanirato, K. Varani, and P.A. Borea Drug Des. Delivery 5 1989 13
3. P.G. Baraldi, R. Budriesi, B. Cacciari, A. Chiarini, L. Garuti, G. Giovanninetti, A. Leoni, and M. Roberti Collect. Czech. Chem. Commun. 1992 169
4. A. Di Stilo, S. Visentin, C. Clara, A.M. Gasco, G. Ermondi, and A. Gasco J. Med. Chem. 41 1998 5393
5. M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, A. Varga, and J. Molnar J. Bioorg. Chem. 10 2002 1051
6. M. Suarez, Y. Verdecia, B. Illescas, R. Martinez-Alvarez, A. Avarez, E. Ochoa, C. Seoane, N. Kayali, and N. Martin Tetrahedron 59 2003 9179
7. R. Shan, C. Velazquez, and E.E. Knaus J. Med. Chem. 47 2004 254
8. Y. Sawada, H. Kayakiri, Y. Abe, T. Mizutani, N. Inamura, M. Asano, C. Hatori, I. Arsmori, T. Oku, and H. Tanaka J. Med. Chem. 47 2004 2853
9. F.R. Buhler, and W. Kiowski J. Hypertens. S3 1987 5
10. J.L. Reid, P.A. Meredith, and F. Pasanisi J. Cardiovasc. Pharmacol. S18 1985 7
11. T. Godfraid, R. Miller, and M. Wibo Pharmacol. Rev. 38 1986 321
12. A. Sausins, and G. Duburs Heterocycles 27 1988 269
13. P.P. Mager, R.A. Coburn, A.J. Solo, D.J. Triggle, and H. Rothe Drug Des. Discovery 8 1992 273
14. R. Mannhold, B. Jablonka, W. Voigdt, K. Schoenafinger, and K. Schravan Eur. J. Med. Chem. 27 1992 229
15. V. Klusa Drugs Future 20 1995 135
16. R.G. Bretzel, C.C. Bollen, E. Maeser, and K.F. Federlin Am. J. Kidney Dis. 21 1993 53
17. R.G. Bretzel, C.C. Bollen, E. Maeser, and K.F. Federlin Drugs Future 17 1992 465
18. R. Boer, and V. Gekeler Drugs Future 20 1995 499
19. B. Love, and K.M. Sander J. Org. Chem. 30 1965 1914
20. Hantzsch Ber. Dtsch. Chem. Ges. 21 1888 942
21. A. Hantzsch Ber. Dtsch. Chem. Ges. 23 1890 1747
22. R.H. Wiley, D.C. England, and L.C. Behr Organic Reactions Vol. 6 1951 John Wiley 367
23. A. Dondoni, A. Massi, E. Minghini, and V. Bertolasi Tetrahedron 60 2004 2311
24. B.M. Khadikar, V.G. Gaikar, and A.A. Chitnavis Tetrahedron Lett. 36 1995 8083
25. L. Ohberg, and J. Westman Synlett 2001 1296
26. A. Agarwal, and P.M.S. Chauhan Tetrahedron Lett. 46 2005 1345
27. S.-J. Ji, Z.-Q. Jiang, J. Lu, and T.-P. Loh Synlett 2004 831
28. R. Sridhar, and P.T. Perumal Tetrahedron 61 2005 2465
29. A.P. Phillips J. Am. Chem. Soc. 71 1949 4003
30. G.J.R. Anderson, and G. Berkelhammer J. Am. Chem. Soc. 80 1958 992
31. H. Singh, D.S.S. Chimni, and S. Kumar Tetrahedron 51 1995 12775
32. M.F. Gordeev, D.V. Patel, and E.M. Gordon J. Org. Chem. 61 1996 924
33. J.G. Breitenbucher, and G. Figliozzi Tetrahedron Lett. 41 2000 4311
34. J.-C. Liang, J.-L. Yeh, C.-S. Wang, S.-F. Liou, C.-H. Tasi, and I.-J. Chen Bioorg. Med. Chem. 10 2002 719
35. R. Miri, H. Niknahad, Gh. Vesal, and A. Shafiee IL Farmaco 57 2002 123
36. A. Dondoni, A. Massi, E. Minghini, S. Sabbatini, and V. Bertoasi J. Org. Chem. 68 2003 6172
37. A. Dondoni, A. Massi, E. Minghini, and V. Bertoasi Tetrahedron 60 2004 2311
38. N. Tewari, N. Dwivedi, and R.P. Tripathi Tetrahedron Lett. 45 2004 9011
39. J.D. Moseley Tetrahedron Lett. 46 2005 3179
40. G. Sabitha, G.S.K.K. Reddy, Ch.S. Reddy, and J.S. Yadav Tetrahedron Lett. 44 2003 4129
41. L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z. Fan, H. Tian, and C.-T. Qian Tetrahedron 61 2005 1539
42. For examples: K.M. Kim, and E.K. Ryu Tetrahedron Lett. 37 1996 1441
43. H. Firouzabadi, N. Iranpoor, and H. Hazarkhani J. Org. Chem. 66 2001 7527
44. K. Ramalinga, P. Vijayalakshmi, and T.N.B. Kaimal Tetrahedron Lett. 43 2002 879
45. H. Firouzabadi, N. Iranpoor, and S. Sobhani Tetrahedron Lett. 43 2002 3653
46. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 43 2002 9703
47. B.P. Bandgar, and K.A. Shaikh Tetrahedron Lett. 44 2003 1959
48. B. Das, J. Banerjee, R. Ramu, R. Pal, N. Ravindranath, and C. Ramesh Tetrahedron Lett. 44 2003 5465
49. R. Saeeng, U. Sirion, P. Sahakitpichan, and M. Isobe Tetrahedron Lett. 44 2003 6211
50. S.-J. Ji, S.-Y. Wang, Y. Zhang, and T.-P. Loh Tetrahedron 60 2004 2051
51. J.S. Yadav, B.V.S. Reddy, S. Shubashree, and K. Sadashiv Tetrahedron Lett. 45 2004 2951
52. P. Phukan J. Org. Chem. 69 2004 4005
53. P. Phukan Tetrahedron Lett. 45 2004 4785
54. J. Sun, Y. Dong, X. Wang, S. Wang, and Y. Hu J. Org. Chem. 69 2004 8932
55. R.S. Bhosale, S.V. Bhosale, S.V. Bhosale, T. Wang, and P.K. Zubaidha Tetrahedron Lett. 45 2004 9111
56. B. Ke, Y. Qin, Q. He, Z. Huang, and F. Wang Tetrahedron Lett. 46 2005 1751
57. B.K. Banik, M. Fernandez, and C. Alvarez Tetrahedron Lett. 46 2005 2479
58. For examples: B.K. Banik, C. Mukhopadhyay, M.S. Venkatraman, and F.F. Becker Tetrahedron Lett. 39 1998 7243
59. B.K. Banik, O. Zegrocka, I. Banik, L. Hackfeld, and F.F. Becker Tetrahedron Lett. 40 1999 6731
60. B.K. Banik, O. Zegrocka, and F.F. Becker J. Chem. Res. (S) 2000 321
61. C. Mukhopadhyay, F.F. Becker, and B.K. Banik J. Chem. Res. (S) 2001 28
62. H. Firouzabadi, N. Iranpoor, and H. Hazarkhani J. Org. Chem. 66 2001 7527
63. J.S. Yadav, B.V.S. Reddy, G. Sabitha, and G.S.K.K. Reddy Synthesis 2000 1532
64. M.K. Basu, M.K. Samajdar, F.F. Becker, and B.K. Banik Synlett 2002 319
65. J.S. Yadav, B.V.S. Reddy, C. Rao, V. Sabitha, and M.J. Reddy Synthesis 2003 247
66. Unpublished results.
67. +) 311.1521, found: 311.1526.