Synthesis and application of silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3- benzimidazoles and bis(indolyl)methanes in water

Journal of Heterocyclic Chemistry

Volumn 48, Issue 6, 2011, Pages 1448-1454

  Veisi, Hojat ^a   Sedrpoushan, Alireza ^b   Zolfigol, Mohammad Ali ^b   Mohanazadeh, Farajollah ^c  

^a PAYAME NOOR UNIVERSITY   (Iran)

^b BU ALI SINA UNIVERSITY   (Iran)

^c IRANIAN RESEARCH ORGANIZATION FOR SCIENCE AND TECHNOLOGY IROST   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; PHENYLENEDIAMINE; SILICON DIOXIDE; SULFONIC ACID DERIVATIVE; TETRABUTYLAMMONIUM; WATER;

ARTICLE; CATALYST; ONE POT SYNTHESIS;

EID: 81855166888     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.765     Document Type: Article

References (89)

1. For recent reviews, see: (a), Bhattacharya, S.; Chaudhuri, P., Curr Med Chem 2008, 15, 1762
2. (b), Horton, D. A.; Bourne, G. T.; Smythe, M. L., Chem Rev 2003, 103, 893
3. (c), Boiani, M.; Gonz'alez, M., Mini-Rev Med Chem 2005, 5, 409.
4. (a), Preston, P. N., Chem Rev 1974, 74, 279
5. (b), Muhaimeed, H. A., J Int Med Res 1997, 25, 175
6. (c), Scott, L. J.; Dunn, C. J.; Mallarkey, G.; Sharp, M., Drugs 2002, 62, 1503
7. (d), Venkatesan, P., J Antimicrob Chemother 1998, 41, 145
8. (e), Shah, D. I.; Sharma, M.; Bansal, Y.; Bansal, G.; Singh, M., Eur J Med Chem 2008, 43, 1808.
9. (a), Denny, W. A.; Rewcastle, G. W.; Baguley, B. C., J Med Chem 1990, 33, 814
10. (b), Labanauskas, L. K.; Brukstus, A. B.; Gaidelis, P. G.; Buchinskaite, V. A.; Udrenaite, E. B.; Dauksas, V. K., Pharm Chem J 2000, 34, 353
11. (c), Sevak, R.; Paul, A.; Goswami, S.; Santini, D., Pharmacol Res 2002, 46, 351.
12. Barker, H. A.; Smyth, R. D.; Weissbach, H.; Toohey, J. I.; Ladd, J. N.; Volcani, B. E., J Biolog Chem 1960, 235, 480.
13. (a), Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J., J Med Chem 1998, 41, 1252
14. (b), Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittneben, H.; Entzeroth, M.; Van Meel, J. C. A.; Wienen, W.; Hauel, N. H., J Med Chem 1993, 36, 4040.
15. (a), Roth, T.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W., Jr.; Michejda, C. J., J Med Chem 1997, 40, 4199
16. (b), Morningstar, M. L.; Roth, T.; Farnsworth, D. W.; Smith, M. K.; Watson, K.; Buckheit, R. W., Jr.; Das, K.; Zhang, W.; Arnold, E.; Julias, J. G.; Hughes, S. H.; Michejda, C. J., J Med Chem 2007, 50, 4003.
17. Takeuchi, K.; Bastian, J. A.; Gifford-Moore, D. S.; Harper, R. W.; Miller, S. C.; Mullaney, J. T.; Sall, D. J.; Smith, G. F.; Zhang, M.; Fisher, M., Bioorg Med Chem Lett 2000, 10, 2347.
18. Göker, H.; Özden, S.; Yildiz, S.; Boykin, D. W., Eur J,. Med Chem 2005, 40, 1062.
19. (a), Smith, J. G.; Ho, I., Tetrahedron Lett 1971, 12, 3541
20. (b), Nagata, K.; Itoh, T.; Ishikawa, H.; Ohsawa, A., Heterocycles 2003, 61, 93
21. (c), Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A., Heterocycles 2004, 63, 2769
22. (d), Perumal, S.; Mariappan, S.; Selvaraj, S., Arkivoc 2004, 8, 46
23. (e), Chakrabarty, M.; Karmakar, S.; Mukherji, A.; Arima, S.; Harigaya, Y., Heterocycles 2006, 68, 967
24. (f), Sun, P.; Hu, Z., J Heterocycl Chem 2006, 43, 773
25. (g), Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Otokesh, S.; Baghbanzadeh, M., Tetrahedron Lett 2006, 47, 2557
26. (h), Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S. R., Tetrahedron Lett 2007, 48, 69
27. (i), Kim, B. H.; Han, R.; Kim, J. S.; Jun, Y. M.; Baik, W.; Lee, B. M., Heterocycles 2004, 63, 41
28. (j), Ghorbani-Vaghei, R.; Veisi, H., Mol Divers 2010, 14, 249
29. (k), Bahrami, K.; Khodaei, M. M.; Nejati, A., Green Chem, to appear.
30. Sundberg, R. J., The Chemistry of Indoles; Academic Press: New York, 1996.
31. Zeligs, M. A., J Med Food 1998, 1, 67.
32. Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y., Tetrahedron Lett 2002, 43, 4075.
33. (a), Bandgar, B. P.; Shaikh, K. A., Tetrahedron Lett 2003, 44, 1959
34. (b), Ramanatham, V. K.; Kotha, V. S. R. S. K.; Kotarkonda, R. G., J Heterocycl Chem 2005, 42, 153.
35. Reddy, A. V.; Ravinder, K.; Reddy, V. L. N.; Venkateshwer Goud, T.; Ravikanth, V.; Venkateswarlu, Y., Synth Commun 2003, 33, 3687.
36. (a), Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z., Chem Rev 2010, 110, 2250
37. (b), Remers, W. A., In Heterocyclic Compounds;, Houlihan, W. J., Ed.; Interscience Publishers: New York, 1972, p 1.
38. Maiti, A. K.; Bhattacharyya, P., J Chem Res 1997, 424.
39. Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R., Tetrahedron Lett 2004, 45, 7729.
40. Firouzabadi, H.; Iranpoor, N.; Jafari, A. A., J Mol Catal A Chem 2005, 244, 168.
41. Deb, M. L.; Bhuyan, P. J., Tetrahedron Lett 2006, 47, 1441.
42. Zhang, Z.-H.; Yin, L.; Wang, Y.-M., Synthesis 2005, 1949.
43. Li, J.-T.; Dai, H.-G.; Xu, W.-Z.; Li, T.-S., Ultrason Sonochem 2006, 13, 24.
44. Bandgar, B. P.; Shaikh, K. A., Tetrahedron Lett 2003, 44, 1959.
45. Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V., Catal Commun 2004, 5, 371.
46. Penieres-Carrillo, G.; García-Estrada, J. G.; Gutiérrez- Ramírez, J. L.; Alvarez-Toledano, C., Green Chem 2003, 5, 337.
47. Ji, S.-J.; Zhou, M.-F.; Gu, D.-G.; Wang, S.-Y.; Loh, T.-P., Synlett 2003, 2077.
48. Mo, L.-P.; Ma, Z.-C.; Zhang, Z.-H., Synth Commun 2005, 35, 1997.
49. Mi, X.; Luo, S.; He, J.; Cheng, J.-P., Tetrahedron Lett 2004, 45, 4567.
50. Kamble, V. T.; Kadam, K. R.; Joshi, N. S.; Muley, D. B., Catal Commun 2007, 8, 498.
51. Pradhan, P. K.; Dey, S.; Giri, V. S.; Jaisankar, P., Synthesis 2005, 1779.
52. Xia, M.; Wang, S. H.; Yuan, W. B., Synth Commun 2004, 34, 3175.
53. Ramesh, C.; Banerjee, J.; Pal, R.; Das, B., Adv Synth Catal 2003, 345, 557.
54. Reddy, B. M.; Sreekanth, P. M.; Lakshmanan, P., J Mol Catal A Chem 2005, 237, 93.
55. Firouzabadi, H.; Iranpoor, N.; Jafarpour, M.; Ghaderi, A., J Mol Catal A Chem 2006, 253, 249.
56. (a), Pore, D. M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P., Arkivoc 2006, 12, 75
57. (b), Zolfigol, M. A.; Salehi, P.; Shiri, M.; Sayadi, A.; Abdoli, A.; Keypour, H.; Rezaeivala, M.; Niknam, K.; Kolvari, E., Mol Divers 2008, 12, 203.
58. Hosseini-Sarvari, M., Acta Chim Slovenica 2007, 54, 354.
59. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Vakilzadeh, Y.; Kiani, S., Monatshefte for Chemie 2007, 138, 595.
60. Hagiwara, H.; Sekifuji, M.; Hoshi, T.; Qiao, K.; Yokoyama, C., Synlett 2007, 1320.
61. Kamble, V. T.; Bandgar, B. P.; Bavikar, S. N., Chin J Chem 2007, 25, 13.
62. Niknam, K.; Zolfigol, M. A.; Sadabadi, T.; Nejati, A., J Iran Chem Soc 2006, 3, 318.
63. Lin, X. F.; Cui, S. L.; Wang, Y. G., Synth Commun 2006, 36, 3153.
64. Zeng, X. F.; Ji, S. J., Lett Org Chem 2006, 3, 374.
65. Zhang, L. P.; Li, Y. Q.; Zhou, M. Y., Chin Chem Lett 2006, 17, 723.
66. Koshima, H.; Matsuaka, W., J Heterocycl Chem 2002, 1089.
67. Khalafi-Nezhad, A.; Parhami, A.; Zare, A.; Moosavi Zare, A. R.; Hasaninejad, A.; Panahi, F., Synthesis 2008, 617.
68. Azizi, N.; Torkian, L.; Saidi, M. R., J Mol Catal A Chem 2007, 275, 109.
69. Mehrazma, S.; Azizi, N.; Saidi, M. R., Lett Org Chem 2006, 3, 161.
70. Zolfigol, M. A.; Salehi, P.; Shiri, M.; Tanbakouchian, Z., Catal Commun 2007, 8, 173.
71. Khodaei, M. M.; Mohammadpoor-Baltork, I.; Memarian, H. R.; Khosropour, A. R.; Nikofar, K.; Ghanbary, P., J Heterocyclic Chem 2008, 45, 1.
72. Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H.; Dehghani-Firouzabadi, A. A., Mol Divers 2010, 14, 87.
73. Ghorbani-Vaghei, R.; Veisi, H., J Braz Chem Soc 2010, 21, 193.
74. (a), Kobayashi, S.; Mori, Y.; Nogayama, S.; Manabe, K., Green Chem 1999, 1, 175
75. (b), Cornils, B., Angew Chem Int Ed Engl 1995, 34, 1575.
76. (a), Zolfigol, M. A., Tetrahedron 2001, 57, 9509
77. (b), Shirini, F.; Zolfigol, M. A.; Salehi, P., Curr Org Chem 2006, 10, 2171
78. (c), Zolfigol, M. A.; Salehi, P.; Shiri, M.; Faal Rastegar, T.; Ghaderi, A., J Iran Chem Soc 2008, 5, 490
79. (d), Zolfigol, M. A.; Hojati, S. F., J Iran Chem Soc 2008, 5, 65
80. (e), Veisi, H., Tetrahedron Lett 2010, 51, 2109.
81. (a), Saunders, D. H.; Barford, R. A.; Magidman, P.; Olszewski, L. T.; Rothbart, H. L., Anal Chem 1974, 46, 834
82. (b), Sharma, S. D.; Konwar, D., Synth Commun 2009, 39, 980
83. (c), Wan, J.-P.; Gan, S.-F.; Wu, J.-M.; Pan, Y., Green Chem 2009, 11, 1633.
84. Bellina, F.; Calanderi, C.; Cauteruccio, S.; Rossi, R., Tetrahedron 2007, 63, 1970.
85. Srinivasa, A. B.; Nandeshwarappa, P.; Kiran, B. M.; Mahadevan, K. M., Phosphorus Sulfur Silicon 2007, 182, 2243.
86. Sadaphal, S. A.; Shelke, K. F.; Sonar, S. S.; Shingare, M. S., Cent Eur J Chem 2008, 6, 622.
87. Waterng, S.-R.; Wang, Q.-Y.; Ding, Y.; Liu, X.-L.; Cai, M.-Z., Catal Lett 2009, 128, 418.
88. (a), Sekiya, M.; Yanaihara, C.; Suzuki, J., Chem Pharm Bull 1969, 17, 752
89. (b), Wang, S.-Y.; Ji, S.-J., Tetrahedron 2006, 62, 1527.