How to cite this paper
Mirjalili, B., Bamoniri, A & Mohaghegh, N. (2013). One-pot synthesis of 2,4,5-tri-substituted-1H-imidazoles promoted by trichloromelamine.Current Chemistry Letters, 2(1), 35-42.
Refrences
1. Eyers, P. A.; Craxton, M.; Morrice, N.; Cohen, P.; Goedert. M. (1998) Conversion of SB 203580-insensitive MAP kinase family members to drug-sensitive forms by a single amino-acid substitution. Chem. Biol., 5, 321-328.
2. Antolini, M.; Bozzoli, A.; Ghiron, C.; Kennedy, G.; Rossi, T.; Ursini, A. (1999) Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. Bioorg. Med. Chem. Lett., 9, 1023-1028.
3. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; Mc Croskey, R. W.; Hannick, S. M.; Gherke L, Credo RB, Hui Y-H, Marsh K, Warner R, Lee JY, Zielinsky-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. (2002) Potent, orally active heterocycle-based combretastatin A-4 analogues:? synthesis, structure?activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation J. Med. Chem., 45, 1697-1711.
4. De Laszlo, S. E.; Hacker, C.; Li, B.; Kim, D.; Mac Coss, M.; Mantl, N.; Pivnichny, J. V.; Colwell, L.; Koch, G. E.; Cascieri, M. A.; Hagmann, W. K. (1999) Potent, orally absorbed glucagon receptor antagonists, Bioorg. Med. Chem. Lett. 9, 641-646.
5. Lambardino, J. C.; Wiseman, E. H. (1974) Preparation and anti inflammatory activity of some nonacidic tri-substituted imidazoles. J. Med. Chem. 17, 1182-1188.
6. Lantos, I.; Zhang, W. Y.; Shiu, X.; Eggleston, D. S. (1993) Synthesis of imidazoles via hetero-Cope rearrangements J. Org. Chem. 58, 7092-7095.
7. Sharma, G.V.; Jyothi, Y.; Lakshmi, P.S. (2006) Efficient room?temperature synthesis of tri? and tetrasubstituted imidazoles catalyzed by ZrCl4, Synth. Commun., 36, 2991-3000.
8. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. (2005) Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-tri-aryl imidazoles from aryl aldehydes and 1, 2-diketones or ?-hydroxyketone. Tetrahedron 61, 3539-3546.
9. Balalaei, S.; Arabanian, A. (2000) One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation, Green Chem. 2, 274-276.
10. Sharma, S.D.; Hazarika, P.; Konwar, D. (2008) An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O, Tetrahedron Lett. 49, 2216-2220.
11. Murthy, S.N.; Madhav, B.; Nageswar, Y.V.D. (2010) DABCO as a mild and efficient catalytic system for the synthesis of highly substituted imidazoles via multi-component condensation strategy, Tetrahedron Lett. 51, 5252-5257.
12. Wang, X. C.; Gong, H.P.; Quan, Z.J.; Li, L.; Ye, H.L. (2009) PEG-400 as an efficient reaction medium for the synthesis of 2,4,5-triaryl-1H-imidazoles and 1, 2,4,5-tetra-aryl-1H-imidazoles. Chinese Chem. Lett. 20, 44-47.
13. Karimi, A. R.; Alimohamadi, Z.; Amini, M. M. (2010) Wells–Dawson heteropolyacid supported on silica: a highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles, Mol. Divers. 14, 635-641.
14. Zang, H.; Su, Q.; Mo, Y.; Cheng, B.-W. Jun, S. (2010) Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles. Ultrason. Sonochem., 17, 749-751.
15. Karimi-Jaberi, Z.; Barekat, M. (2010) One-pot synthesis of tri-and tetra-substituted imidazoles using sodium dihydrogen phosphate under solvent-free conditions.Chinese Chem. Lett. 21, 1183-1186.
16. Shaterian, H. R.; Ranjbar, M. (2011) An environmental friendly approach for the synthesis of highly substituted imidazoles using Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst. J. Mol. Liquid. 160, 40-49.
17. Teimouri, A.; Najafi Chermahini, A. (2011) An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles catalyzed via solid acid nano-catalyst. J. Mol. Catal. A: Chem. 346, 39-45.
18. Chary, M.V.; Keerthysri, N.C.; Vupallapati, S.V.N.; Lingaiah,N.; Kantevari, S. (2008) Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles. Catal. Commun. 9, 2013-2017.
19. Safari, J.; DehghanKhalili, S.; Banitaba, S. H. (2010) A novel and an efficient catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles by using microwave irradiation under solvent-free conditions. J. Chem. Sci., 122, 437-441.
20. Safari, J.; DehghanKhalili, S.; Rezaei, M.; Banitaba, S. H. Meshkani, F. (2010) Nanocrystalline Magnesium Oxide: A novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives (III). Monatsh. Chem. 141, 1339-1345.
21. Joshi, R.S.; Mandhane, P. G.; Shaikh,M. U.; Kale, R. P.; Gill, C. H. (2010) Potassium dihydrogen phosphate catalyzed one-pot synthesis of 2,4,5-triaryl-1H-imidazoles. Chinese Chem. Lett., 21, 429-431
22. Bamoniri, A.; Zolfigol, M. A.; Mirjalili, B. F.; Fallah, F. (2007) Efficient procedure for chemoselective n-nitrosation of secondary amines with trichloromelamine–NaNO2 Russian J. Org. Chem., 43, 1393-1396
23. Mirjalili, B. F.; Bamoniri, A.; Akrami, H. R. (2009) Trichloromelamine/ Zr(HSO4)4/KBr: an efficient heterogeneous alternative for oxidation of alcohols and diols. Digest J. Nanomat. Biostruct., 4, 763-767.
24. Mirjalili, B. F.; Bamoniri, A.; Amrollahi, M. A.; Dastan, E. (2009) Trichloromelamine and triphenylphosphine as a versatile and efficient system for oxidation of alcohols under solvent-free condition. Iran. J. Org. Chem. 1, 13-17.
25. Ghorbani-Ch, A.; Amani, K.; Zolfigol, M. A.; Hajjami, M.; Ayazi-Nasrabadi, R. (2009) 1, 3-Dichloro-5, 5-dimethylhydantoin (DCH) and trichloromelamine (TCM) as efficient catalysts for the chemoselective trimethylsilylation of hydroxyl group with 1, 1,1,3,3,3-hexamethyldisilazane (HMDS) under mild conditions. J. Chinese Chem. Soc., 56, 255-260.
26. Mirjalili, B.F.; Bamoniri, A.; Akbari. (2008) BF3•SiO2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. Tetrahedron Lett., 49, 6454-6456.
27. Sadeghi, B.; Mirjalili, B. F.; Hashemi, M.M. (2008) BF3.SiO2: An efficient heterogeneous alternative for regio-chemo and stereoselective claisen-schmidt condensation. J. Iran. Chem. Soc., 5, 694-698.
28. Mirjalili, B.F.; Bamoniri, A.; Akbari, A. (2011) One-Pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones (thiones) promoted by nano-BF3.SiO2. J. Iran. Chem. Soc., 8, S135-S140.
29. Sadeghi, B.; Mirjalili, B.F.; Hashemi, M.M. (2008) BF3•SiO2: an efficient reagent system for the one-pot synthesis of 1, 2,4,5-tetrasubstituted imidazoles. Tetrahedron Lett., 49, 2575-2577.
30. Mirjalili, B. F.; Bamoniri, A.; Akbari, A. (2011) Nano-BF3•SiO2: a reusable and eco-friendly catalyst for synthesis of quinoxalines. Chem. Heterocycl. Comp., 47, 487-491.
31. Samai, S.; Nandi, G.C.;Singh, P.; Singh, M.S. (2009) L-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles. Tetrahedron, 65, 10155-10161.
2. Antolini, M.; Bozzoli, A.; Ghiron, C.; Kennedy, G.; Rossi, T.; Ursini, A. (1999) Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. Bioorg. Med. Chem. Lett., 9, 1023-1028.
3. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; Mc Croskey, R. W.; Hannick, S. M.; Gherke L, Credo RB, Hui Y-H, Marsh K, Warner R, Lee JY, Zielinsky-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. (2002) Potent, orally active heterocycle-based combretastatin A-4 analogues:? synthesis, structure?activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation J. Med. Chem., 45, 1697-1711.
4. De Laszlo, S. E.; Hacker, C.; Li, B.; Kim, D.; Mac Coss, M.; Mantl, N.; Pivnichny, J. V.; Colwell, L.; Koch, G. E.; Cascieri, M. A.; Hagmann, W. K. (1999) Potent, orally absorbed glucagon receptor antagonists, Bioorg. Med. Chem. Lett. 9, 641-646.
5. Lambardino, J. C.; Wiseman, E. H. (1974) Preparation and anti inflammatory activity of some nonacidic tri-substituted imidazoles. J. Med. Chem. 17, 1182-1188.
6. Lantos, I.; Zhang, W. Y.; Shiu, X.; Eggleston, D. S. (1993) Synthesis of imidazoles via hetero-Cope rearrangements J. Org. Chem. 58, 7092-7095.
7. Sharma, G.V.; Jyothi, Y.; Lakshmi, P.S. (2006) Efficient room?temperature synthesis of tri? and tetrasubstituted imidazoles catalyzed by ZrCl4, Synth. Commun., 36, 2991-3000.
8. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. (2005) Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-tri-aryl imidazoles from aryl aldehydes and 1, 2-diketones or ?-hydroxyketone. Tetrahedron 61, 3539-3546.
9. Balalaei, S.; Arabanian, A. (2000) One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation, Green Chem. 2, 274-276.
10. Sharma, S.D.; Hazarika, P.; Konwar, D. (2008) An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O, Tetrahedron Lett. 49, 2216-2220.
11. Murthy, S.N.; Madhav, B.; Nageswar, Y.V.D. (2010) DABCO as a mild and efficient catalytic system for the synthesis of highly substituted imidazoles via multi-component condensation strategy, Tetrahedron Lett. 51, 5252-5257.
12. Wang, X. C.; Gong, H.P.; Quan, Z.J.; Li, L.; Ye, H.L. (2009) PEG-400 as an efficient reaction medium for the synthesis of 2,4,5-triaryl-1H-imidazoles and 1, 2,4,5-tetra-aryl-1H-imidazoles. Chinese Chem. Lett. 20, 44-47.
13. Karimi, A. R.; Alimohamadi, Z.; Amini, M. M. (2010) Wells–Dawson heteropolyacid supported on silica: a highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles, Mol. Divers. 14, 635-641.
14. Zang, H.; Su, Q.; Mo, Y.; Cheng, B.-W. Jun, S. (2010) Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles. Ultrason. Sonochem., 17, 749-751.
15. Karimi-Jaberi, Z.; Barekat, M. (2010) One-pot synthesis of tri-and tetra-substituted imidazoles using sodium dihydrogen phosphate under solvent-free conditions.Chinese Chem. Lett. 21, 1183-1186.
16. Shaterian, H. R.; Ranjbar, M. (2011) An environmental friendly approach for the synthesis of highly substituted imidazoles using Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst. J. Mol. Liquid. 160, 40-49.
17. Teimouri, A.; Najafi Chermahini, A. (2011) An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles catalyzed via solid acid nano-catalyst. J. Mol. Catal. A: Chem. 346, 39-45.
18. Chary, M.V.; Keerthysri, N.C.; Vupallapati, S.V.N.; Lingaiah,N.; Kantevari, S. (2008) Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles. Catal. Commun. 9, 2013-2017.
19. Safari, J.; DehghanKhalili, S.; Banitaba, S. H. (2010) A novel and an efficient catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles by using microwave irradiation under solvent-free conditions. J. Chem. Sci., 122, 437-441.
20. Safari, J.; DehghanKhalili, S.; Rezaei, M.; Banitaba, S. H. Meshkani, F. (2010) Nanocrystalline Magnesium Oxide: A novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives (III). Monatsh. Chem. 141, 1339-1345.
21. Joshi, R.S.; Mandhane, P. G.; Shaikh,M. U.; Kale, R. P.; Gill, C. H. (2010) Potassium dihydrogen phosphate catalyzed one-pot synthesis of 2,4,5-triaryl-1H-imidazoles. Chinese Chem. Lett., 21, 429-431
22. Bamoniri, A.; Zolfigol, M. A.; Mirjalili, B. F.; Fallah, F. (2007) Efficient procedure for chemoselective n-nitrosation of secondary amines with trichloromelamine–NaNO2 Russian J. Org. Chem., 43, 1393-1396
23. Mirjalili, B. F.; Bamoniri, A.; Akrami, H. R. (2009) Trichloromelamine/ Zr(HSO4)4/KBr: an efficient heterogeneous alternative for oxidation of alcohols and diols. Digest J. Nanomat. Biostruct., 4, 763-767.
24. Mirjalili, B. F.; Bamoniri, A.; Amrollahi, M. A.; Dastan, E. (2009) Trichloromelamine and triphenylphosphine as a versatile and efficient system for oxidation of alcohols under solvent-free condition. Iran. J. Org. Chem. 1, 13-17.
25. Ghorbani-Ch, A.; Amani, K.; Zolfigol, M. A.; Hajjami, M.; Ayazi-Nasrabadi, R. (2009) 1, 3-Dichloro-5, 5-dimethylhydantoin (DCH) and trichloromelamine (TCM) as efficient catalysts for the chemoselective trimethylsilylation of hydroxyl group with 1, 1,1,3,3,3-hexamethyldisilazane (HMDS) under mild conditions. J. Chinese Chem. Soc., 56, 255-260.
26. Mirjalili, B.F.; Bamoniri, A.; Akbari. (2008) BF3•SiO2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. Tetrahedron Lett., 49, 6454-6456.
27. Sadeghi, B.; Mirjalili, B. F.; Hashemi, M.M. (2008) BF3.SiO2: An efficient heterogeneous alternative for regio-chemo and stereoselective claisen-schmidt condensation. J. Iran. Chem. Soc., 5, 694-698.
28. Mirjalili, B.F.; Bamoniri, A.; Akbari, A. (2011) One-Pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones (thiones) promoted by nano-BF3.SiO2. J. Iran. Chem. Soc., 8, S135-S140.
29. Sadeghi, B.; Mirjalili, B.F.; Hashemi, M.M. (2008) BF3•SiO2: an efficient reagent system for the one-pot synthesis of 1, 2,4,5-tetrasubstituted imidazoles. Tetrahedron Lett., 49, 2575-2577.
30. Mirjalili, B. F.; Bamoniri, A.; Akbari, A. (2011) Nano-BF3•SiO2: a reusable and eco-friendly catalyst for synthesis of quinoxalines. Chem. Heterocycl. Comp., 47, 487-491.
31. Samai, S.; Nandi, G.C.;Singh, P.; Singh, M.S. (2009) L-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1, 2,4,5-tetrasubstituted imidazoles. Tetrahedron, 65, 10155-10161.