Synthesis of 1,2,4,5-Tetrasubstituted imidazoles using sulfuric acid ([3-(3-Silicapropyl)sulfanyl]propyl]ester as a recyclable solid acid

Journal of Heterocyclic Chemistry

Volumn 49, Issue 3, 2012, Pages 634-639

  Tavakoli, Ziba ^a   Bagherneghad, Mojtaba ^a   Niknam, Khodabakhsh ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4,5 TETRASUBSTITUTED IMIDAZOLE; ALDEHYDE; AMINE; AMMONIUM ACETATE; BENZILIC ACID; IMIDAZOLE DERIVATIVE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; SYNTHESIS;

EID: 84863822570     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.847     Document Type: Article

References (54)

1. Heers, J.,;, Backx, L. J. J.,;, Mostmans, J. H.,;, Van Cutsem, J., J Med Chem 1979, 22, 1003.
2. (a), Hunkeler, W.,;, Mohler, H.,;, Pieri, L.,;, Polc, P.,;, Bonetti, E. P.,;, Cumin, R.,;, Schaffner, R.,;, Haefely, W., Nature 1981, 290, 514
3. (b), Brimblecombe, R. W.,;, Duncan, W. A. M.,;, Durant, G. J.,;, Emmett, J. C.,;, Ganellin, C. R.,;, Parons, M. E., J Int Med Res 1975, 3, 86
4. (c), Tanigawara, Y.,;, Aoyama, N.,;, Kita, T.,;, Shirakawa, K.,;, Komada, F.,;, Kasuga, M.,;, Okumura, K., Clin Pharmacol Ther 1999, 66, 528
5. (d), Wauquier, A.,;, Van Den Broeck, W. A. E.,;, Verheyen, J. L.,;, Janssen, P. A. J., Eur J Pharmacol 1978, 47, 367.
6. (a), Antolini, M.,;, Bozzoli, A.,;, Ghiron, C.,;, Kennedy, G.,;, Rossi, T.,;, Ursini, A., Bioorg Med Chem Lett 1999, 9, 1023
7. (b), Wang, L.,;, Woods, K. W.,;, Li, Q.,;, Barr, K. J.,;, McCroskey, R. W.,;, Hannick, S. M.,;, Gherke, L.,;, Credo, R. B.,;, Hui, Y.-H.,;, Marsh, K.,;, Warner, R.,;, Lee, J. Y.,;, Zielinsky-Mozng, N.,;, Frost, D.,;, Rosenberg, S. H.,;, Sham, H. L., J Med Chem 2002, 45, 1697.
8. (a), Lee, J. C.,;, Laydon, J. T.,;, McDonnell, P. C.,;, Gallagher, T. F.,;, Kumar, S.,;, Green, D.,;, McNulty, D.,;, Blumenthal, M. J.,;, Keys, J. R.,;, Vatter, S. W. L.,;, Strickler, J. E.,;, McLaughlin, M. M.,;, Siemens, I. R.,;, Fisher, S. M.,;, Livi, G. P.,;, White, J. R.,;, Adams, J. L.,;, Young, P. R., Nature 1994, 372, 739
9. (b), Takle, A. K.,;, Brown, M. J. B.,;, Davies, S.,;, Dean, D. K.,;, Francis, G.,;, Gaiba, A.,;, Hird, A. W.,;, King, F. D.,;, Lovell, P. J.,;, Naylor, A.,;, Reith, A. D.,;, Steadman, J. G.,;, Wilson, D. M., Bioorg Med Chem Lett 2006, 16, 378.
10. de Laszlo, S. E.,;, Hacker, C.,;, Li, B.,;, Kim, D.,;, MacCoss, M.,;, Mantalo, N.,;, Pivnichny, J. V.,;, Colwell, L.,;, Koch, G. E.,;, Cascieri, M. A.,;, Hagmenn, W. K., Bioorg Med Chem Lett 1999, 9, 641.
11. (a), Schmierer, R.,;, Mildenberger, H.,;, Buerstell, H., Ger. Pat. 3,61,464 (1987)
12. (b), Schmierer, R.,;, Mildenberger, H.,;, Buerstell, H., Chem Abstr 1988, 108, 37838.
13. (a), Maier, T.,;, Schmierer, R.,;, Bauer, K.,;, Bieringer, H.,;, Buerstell, H.,;, Sachse, B., U.S. Pat. 4,820,335 (1989)
14. (b), Maier, T.,;, Schmierer, R.,;, Bauer, K.,;, Bieringer, H.,;, Buerstell, H.,;, Sachse, B., Chem Abstr 1989, 111, 19494w.
15. (a), Siamaki, A. R.,;, Arndtsen, B. A., J Am Chem Soc 2006, 128, 6050
16. (b), Frantz, D. E.,;, Morency, L.,;, Soheili, A.,;, Murry, J. A.,;, Grabowski, E. J. J.,;, Tillyer, R. D., Org Lett 2004, 6, 843-846.
17. (a), Evans, D. A.,;, Lundy, K. M., J Am Chem Soc 1992, 114, 1495
18. (b), Davidson, D.,;, Weiss, M.,;, Jelling, M., J Org Chem 1937, 2, 319
19. (c), Claiborne, C. F.,;, Liverton, N. J.,;, Nguyen, K. T., Tetrahedron Lett 1998, 39, 8939.
20. Schubert, H.,;, Stodolka, H., J Prakt Chem 1963, 22, 130.
21. Heravi, M. M.,;, Derikvand, F.,;, Bamoharram, F. F., J Mol Catal A Chem 2007, 263, 112.
22. Balalaie, S.,;, Arabanian, A., Green Chem 2000, 2, 274.
23. Usyatinsky, A. Y.,;, Khmelnitsky, Y. L., Tetrahedron Lett 2000, 41, 5031.
24. Karimi, A. R.,;, Alimohammadi, Z.,;, Azizian, J.,;, Mohammadi, A. A.,;, Mohammadizadeh, M. R., Catal Commun 2006, 7, 728.
25. Kantevari, S.,;, Vuppalapati, S. V. N.,;, Biradar, D. O.,;, Nagarapu, L., J Mol Catal A: Chem 2007, 266, 109.
26. (a), Kidwai, M.,;, Mothsra, P.,;, Bansal, V.,;, Somvanshi, R. K.,;, Ethayathulla, A. S.,;, Dey, S.,;, Singh, T. P., J Mol Catal A: Chem 2007, 265, 177
27. (b), Ren, Y. M.,;, Cai, C., J Chem Res (s) 2010, 133.
28. Heravi, M. M.,;, Derikv, F.,;, Haghighi, M., Monatsh Chem 2008, 139, 31.
29. Sadeghi, B.,;, Mirjalili, B. B. F.,;, Hashemi, M. M., Tetrahedron Lett 2008, 49, 2575.
30. Sharma, S. D.,;, Hazarika, P.,;, Konwar, D., Tetrahedron Lett 2008, 49, 2216.
31. Nagarapu, L.,;, Apuri, S.,;, Kantevari, S., J Mol Catal A: Chem 2007, 266, 104.
32. Lipshutz, B. H.,;, Morey, M. C., J Org Chem 1983, 48, 3745.
33. Mohammadizadeh, M. R.,;, Hasaninejad, A.,;, Bahramzadeh, M., Synth Commun 2009, 39, 3232.
34. (a), Samai, S.,;, Nandi, G. C.,;, Singh, P.,;, Singh, M. S., Tetrahedron 2009, 65, 10155
35. (b), Li, J. J.,;, Lin, S. W.,;, Dai, J. J.,;, Su, W. K., J Chem Res (s) 2010, 196.
36. Sivakumar, K.,;, Kathirvel, A.,;, Lalitha, A., Tetrahedron Lett 2010, 51, 3018.
37. Mukhopadhyay, C.,;, Tapaswi, P. K.,;, Drew, M. G. B., Tetrahedron Lett 2010, 51, 3944.
38. Davoodnia, A.,;, Heravi, M. M.,;, Safavi-Rad, Z.,;, Tavakoli-Hoseini, N., Synth Commun 2010, 40, 2588.
39. Hekmat Shoar, R.,;, Rahimzadeh, G.,;, Derikvand, F.,;, Farzaneh, M., Synth Commun 2010, 40, 1270.
40. (a), Karimi, B.,;, Ghoreishi-Nezhad, M., J Mol Catal A: Chem 2007, 277, 262
41. (b), Zareyee, D.,;, Karimi, B., Tetrahedron Lett 2007, 48, 1277.
42. (a), Melero, J. A.,;, Grieken, R. V.,;, Morales, G., Chem Rev 2006, 106, 3790
43. (b), Shimizu, V,;, Hayashi, E.,;, Hatamachi, T.,;, Kodama, T.,;, Higuch, T.,;, Satsuma, A.,;, Kitayama, Y., J Catal 2005, 231, 131.
44. Niknam, K.,;, Saberi, D., Appl Catal A: Gen 2009, 366, 220.
45. Niknam, K.,;, Saberi, D., Tetrahedron Lett 2009, 50, 5210.
46. (a), Niknam, K.,;, Saberi, D.,;, Nouri Sefat, M., Tetrahedron Lett 2009, 50, 4058
47. (b), Niknam, K.,;, Saberi, D.,;, Mohagheghnejad, M., Molecules 2009, 14, 1915
48. (c), Niknam, K.,;, Saberi, D.,;, Baghernejad, M., Chin Chem Lett 2009, 20, 1444
49. (d), Niknam, K.,;, Saberi, D.,;, Sadegheyan, M.,;, Deris, A., Tetrahedron Lett 2010, 51, 962
50. (e), Niknam, K.,;, Saberi, D.,;, Molaee, H.,;, Zolfigol, M. A., Can J Chem 2010, 88, 164
51. (f), Niknam, K.,;, Saberi, D.,;, Baghernejad, M., Phosphorus Sulfur Silicon 2010, 185, 875
52. (g), Niknam, K.,;, Panahi, F.,;, Saberi, D.,;, Mohagheghnejad, M., J Heterocycl Chem 2010, 47, 292.
53. (a), Gelens, E.,;, De Kanter, F. J. J.,;, Schmitz, R. F.,;, Sliedregt, L. A.,;, Van Steen, B. J.,;, Kruse, C. G.,;, Leurs, R.,;, Groen, M. B.,;, Orru, R. V., Mol Div 2006, 10, 17
54. (b), Siddiqui, S. A.,;, Narkhede, U. C.,;, Palimkar, S. S.,;, Daniel, T.,;, Lahoti, R. J.,;, Srinivasan, K. V., Tetrahedron 2005, 61, 3539.