메뉴 건너뛰기




Volumn 44, Issue 15, 2014, Pages 2256-2268

Design and Optimization of Ecofriendly One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles by Three-Component Condensation Using Response Surface Methodology

Author keywords

2,4,5 triaryl 1 H imidazole; Phase transfer catalysts; Radziszewski reaction; response surface method

Indexed keywords

4,5 DIPHENYL 2 NITROPHENYL 1H IMIDAZOLE; ACETIC ACID; BIPHENYL; IMIDAZOLE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 84902961524     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2014.893359     Document Type: Article
Times cited : (16)

References (37)
  • 1
    • 0037238724 scopus 로고    scopus 로고
    • Multicomponent reactions: Emerging chemistry in drug discovery from xylocain to crixivan
    • Hulme, C.; Gore, V. Multicomponent reactions: Emerging chemistry in drug discovery from xylocain to crixivan. Curr. Med. Chem. 2003, 10(1), 51.
    • (2003) Curr. Med. Chem. , vol.10 , Issue.1 , pp. 51
    • Hulme, C.1    Gore, V.2
  • 7
    • 78650106119 scopus 로고    scopus 로고
    • Synthesis and anthelmintic activity of some novel 2-substituted-4,5- diphenyl imidazoles
    • Dutta, S. Synthesis and anthelmintic activity of some novel 2-substituted-4,5-diphenyl imidazoles. Acta Pharm. 2010, 60(2), 229.
    • (2010) Acta Pharm. , vol.60 , Issue.2 , pp. 229
    • Dutta, S.1
  • 9
    • 43049150549 scopus 로고    scopus 로고
    • Synthesis, spectral and antimicrobial studies on some newer imidazole analogs
    • Dahiya, R. Synthesis, spectral and antimicrobial studies on some newer imidazole analogs. Sci. Pharm. 2008, 76(2), 217.
    • (2008) Sci. Pharm. , vol.76 , Issue.2 , pp. 217
    • Dahiya, R.1
  • 10
    • 0035821386 scopus 로고    scopus 로고
    • Regiospecific synthesis of 2,3-disubstituted-Lhistidines and histamines
    • Narayanan, S.; Vangapandu, S.; Jain, R. Regiospecific synthesis of 2,3-disubstituted-Lhistidines and histamines. Bioorg. Med. Chem. Lett. 2001, 11(9), 1133.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , Issue.9 , pp. 1133
    • Narayanan, S.1    Vangapandu, S.2    Jain, R.3
  • 11
    • 0037450422 scopus 로고    scopus 로고
    • A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation
    • Balalaie, S.; Hashemi, M. M.; Akhbari, M. A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation. Tetrahedron Lett. 2003, 44(8), 1709.
    • (2003) Tetrahedron Lett. , vol.44 , Issue.8 , pp. 1709
    • Balalaie, S.1    Hashemi, M.M.2    Akhbari, M.3
  • 12
    • 0034709637 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions
    • Usyatinsky, A. Y.; Khemelnitsky, Y. L. Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions. Tetrahedron Lett. 2000, 41(26), 5031.
    • (2000) Tetrahedron Lett. , vol.41 , Issue.26 , pp. 5031
    • Usyatinsky, A.Y.1    Khemelnitsky, Y.L.2
  • 13
    • 2442428407 scopus 로고    scopus 로고
    • Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation
    • Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation. Org. Lett. 2004, 6(9), 1453.
    • (2004) Org. Lett. , vol.6 , Issue.9 , pp. 1453
    • Wolkenberg, S.E.1    Wisnoski, D.D.2    Leister, W.H.3    Wang, Y.4    Zhao, Z.5    Lindsley, C.W.6
  • 14
    • 14844342306 scopus 로고    scopus 로고
    • Room-temperature ionic liquid-promoted improved and rapid synthesis of 2,4,5- triaryl imidazoles from aryl aldehydes and 1,2-diketones or a-hydroxyketone
    • Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Room-temperature ionic liquid-promoted improved and rapid synthesis of 2,4,5- triaryl imidazoles from aryl aldehydes and 1,2-diketones or a-hydroxyketone. Tetrahedron 2005, 61(14), 3539.
    • (2005) Tetrahedron , vol.61 , Issue.14 , pp. 3539
    • Siddiqui, S.A.1    Narkhede, U.C.2    Palimkar, S.S.3    Daniel, T.4    Lahoti, R.J.5    Srinivasan, K.V.6
  • 15
    • 33846813598 scopus 로고    scopus 로고
    • Highly efficient four-component onepot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts
    • Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. Highly efficient four-component onepot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts. J. Mol. Catal. A: Chem. 2007, 263(1-2), 112.
    • (2007) J. Mol. Catal. A: Chem. , vol.263 , Issue.1-2 , pp. 112
    • Heravi, M.M.1    Derikvand, F.2    Bamoharram, F.F.3
  • 16
    • 64149092934 scopus 로고    scopus 로고
    • Polymer-supported zinc chloride: A highly active and reusable heterogeneous catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles
    • Wang, L.; Cai, C. Polymer-supported zinc chloride: A highly active and reusable heterogeneous catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles. Monatsh. Chem. 2009, 140(5), 541.
    • (2009) Monatsh. Chem. , vol.140 , Issue.5 , pp. 541
    • Wang, L.1    Cai, C.2
  • 17
    • 0034389275 scopus 로고    scopus 로고
    • Zeolite HY and silica gel as new and efficient heterogenous catalysts for the synthesis of triarylimidazoles under microwave irradiation
    • Balalaie, S.; Arabanian, A.; Hashtroudi, M. Zeolite HY and silica gel as new and efficient heterogenous catalysts for the synthesis of triarylimidazoles under microwave irradiation. Mont. Fur. Chem. 2000, 131(9), 945.
    • (2000) Mont. Fur. Chem. , vol.131 , Issue.9 , pp. 945
    • Balalaie, S.1    Arabanian, A.2    Hashtroudi, M.3
  • 18
    • 84863650486 scopus 로고    scopus 로고
    • A novel polymeric catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles
    • Mohammadi, A.; Keshvari, H.; Sandroos, R.; Rouhi, H.; Sepehr, Z. A novel polymeric catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles. J. Chem. Sci. 2012, 124(3), 717.
    • (2012) J. Chem. Sci. , vol.124 , Issue.3 , pp. 717
    • Mohammadi, A.1    Keshvari, H.2    Sandroos, R.3    Rouhi, H.4    Sepehr, Z.5
  • 19
    • 84856143985 scopus 로고    scopus 로고
    • Metal chloride hydrates as Lewis acid catalysts in multicomponent synthesis of 2,4,5-triarylimidazoles or 2,4,5- triaryloxazoles
    • Marcelo, V. M.; Marcelo, M. R.; Luiz, A. M. F.; Dennis, R. Metal chloride hydrates as Lewis acid catalysts in multicomponent synthesis of 2,4,5-triarylimidazoles or 2,4,5- triaryloxazoles. J. Braz. Chem. Soc. 2012, 23(1), 171.
    • (2012) J. Braz. Chem. Soc. , vol.23 , Issue.1 , pp. 171
    • Marcelo, V.M.1    Marcelo, M.R.2    Luiz, A.M.F.3    Dennis, R.4
  • 20
    • 40049097415 scopus 로고    scopus 로고
    • An efficient and one-pot synthesis of 2,4,5- trisubstituted imidazoles catalysed by InCl3 3H2O
    • Sharma, S. D.; Hazarika, P.; Konwar, D. An efficient and one-pot synthesis of 2,4,5- trisubstituted imidazoles catalysed by InCl3 3H2O. Tetrahedron Lett. 2008, 49(14), 2216.
    • (2008) Tetrahedron Lett. , vol.49 , Issue.14 , pp. 2216
    • Sharma, S.D.1    Hazarika, P.2    Konwar, D.3
  • 21
    • 34548720422 scopus 로고    scopus 로고
    • P-TSA catalysed synthesis of 2,4,5- triarylimidazoles from ammonium heptamolybdate tetrahydrate in TBAI
    • Mohammad, M. K.; Bahrami, K.; Iman, K. p-TSA catalysed synthesis of 2,4,5- triarylimidazoles from ammonium heptamolybdate tetrahydrate in TBAI. J. Chin. Chem. Soc. 2007, 54(4), 829.
    • (2007) J. Chin. Chem. Soc. , vol.54 , Issue.4 , pp. 829
    • Mohammad, M.K.1    Bahrami, K.2    Iman, K.3
  • 22
    • 36849056612 scopus 로고    scopus 로고
    • Sulphanilic acid- catalysed facile one-pot synthesis of 2,4,5-triarylimidazoles from benzyl=benzoin and aromatic aldehydes
    • Mohammed, A. F.; Kokare, N. D.; Sangshetti, J. N.; Shinde, D. B. Sulphanilic acid- catalysed facile one-pot synthesis of 2,4,5-triarylimidazoles from benzyl=benzoin and aromatic aldehydes. J. Korean Chem. Soc. 2007, 51(5), 418.
    • (2007) J. Korean Chem. Soc. , vol.51 , Issue.5 , pp. 418
    • Mohammed, A.F.1    Kokare, N.D.2    Sangshetti, J.N.3    Shinde, D.B.4
  • 23
  • 24
    • 0037147973 scopus 로고    scopus 로고
    • Efficient and environmentally friendly synthesis of 2-amino-imidazole
    • Weinmann, H.; Harre, M.; Koeing, K.; Merten, E.; Tilestam, U. Efficient and environmentally friendly synthesis of 2-amino-imidazole. Tetrahedron Lett. 2002, 43(4), 593.
    • (2002) Tetrahedron Lett. , vol.43 , Issue.4 , pp. 593
    • Weinmann, H.1    Harre, M.2    Koeing, K.3    Merten, E.4    Tilestam, U.5
  • 25
    • 0346121670 scopus 로고    scopus 로고
    • A modified procedure for the synthesis of 1-arylimidazoles
    • Liu, J.; Chem, J.; Zhao, J.; Li, L.; Zhang, H. A modified procedure for the synthesis of 1-arylimidazoles. Synthesis 2003, 17, 2661.
    • (2003) Synthesis , vol.17 , pp. 2661
    • Liu, J.1    Chem, J.2    Zhao, J.3    Li, L.4    Zhang, H.5
  • 26
    • 38949150338 scopus 로고    scopus 로고
    • Sodium bisulphate as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzyl or benzoin and aromatic aldehydes
    • Sangshetti, J. N.; Shinde, D. B.; Kokare, N. D.; Kotharkar, S. A. Sodium bisulphate as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzyl or benzoin and aromatic aldehydes. Monatsh. Chem. 2008, 139(2), 125.
    • (2008) Monatsh. Chem. , vol.139 , Issue.2 , pp. 125
    • Sangshetti, J.N.1    Shinde, D.B.2    Kokare, N.D.3    Kotharkar, S.A.4
  • 27
    • 53849139123 scopus 로고    scopus 로고
    • Cerric ammonium nitrate-catalyzed three-component one-pot efficient synthesis of 2,4,5-triaryl-1Himidazoles
    • Sangshetti, J. N.; Kokare, N. D.; Kotharkara, S. A.; Shinde, D. B. Cerric ammonium nitrate-catalyzed three-component one-pot efficient synthesis of 2,4,5-triaryl-1Himidazoles. J. Chem. Sci. 2008, 120(5), 463.
    • (2008) J. Chem. Sci. , vol.120 , Issue.5 , pp. 463
    • Sangshetti, J.N.1    Kokare, N.D.2    Kotharkara, S.A.3    Shinde, D.B.4
  • 28
    • 57449091360 scopus 로고    scopus 로고
    • Tandem oxidation process using cerric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions
    • Shaabani, A.; Mleki, A.; Behnam, M. Tandem oxidation process using cerric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions. Synth. Commun. 2008, 39(1), 102.
    • (2008) Synth. Commun. , vol.39 , Issue.1 , pp. 102
    • Shaabani, A.1    Mleki, A.2    Behnam, M.3
  • 29
    • 33750948229 scopus 로고    scopus 로고
    • Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate
    • Wang, L.; Wang, Y.; Tian, H.; Yao, Y.; Shao, J.; Liu, B. Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate. J. Fluorine Chem. 2006, 127(12), 1570.
    • (2006) J. Fluorine Chem. , vol.127 , Issue.12 , pp. 1570
    • Wang, L.1    Wang, Y.2    Tian, H.3    Yao, Y.4    Shao, J.5    Liu, B.6
  • 30
    • 49049120484 scopus 로고    scopus 로고
    • Potassium aluminum sulfate (alum): An efficient catalyst for the one-pot synthesis of trisubstituted imidazoles
    • Mohamadi, A. A.; Mivechi, M.; Kefayati, H. Potassium aluminum sulfate (alum): An efficient catalyst for the one-pot synthesis of trisubstituted imidazoles. Montash. Chem. 2008, 139(8), 935.
    • (2008) Montash. Chem. , vol.139 , Issue.8 , pp. 935
    • Mohamadi, A.A.1    Mivechi, M.2    Kefayati, H.3
  • 31
    • 70350516103 scopus 로고    scopus 로고
    • L-proline: An efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
    • Samai, S.; Nandi, G. C.; Singh, P.; Singh, M. S. L-proline: An efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. Tetrahedron 2009, 65(49), 10155.
    • (2009) Tetrahedron , vol.65 , Issue.49 , pp. 10155
    • Samai, S.1    Nandi, G.C.2    Singh, P.3    Singh, M.S.4
  • 33
    • 0033613520 scopus 로고    scopus 로고
    • Phase-transfer catalysis: Some important applications in organic synthesis
    • Albanese, D.; Landini, D.; Maia, A.; Penso, M. Phase-transfer catalysis: Some important applications in organic synthesis. J. Mol. Catal. A: Chem. 1999, 150(1-2), 113.
    • (1999) J. Mol. Catal. A: Chem. , vol.150 , Issue.1-2 , pp. 113
    • Albanese, D.1    Landini, D.2    Maia, A.3    Penso, M.4
  • 36
    • 13844298043 scopus 로고    scopus 로고
    • Optimization of ethyl(2-phthlylimidoethoxy) acetate synthesis with the aid of DOE
    • Synoradzki, L.; Janczewski, D.; Wlostowski, M. Optimization of ethyl(2-phthlylimidoethoxy) acetate synthesis with the aid of DOE. Org. Process Res. Dev. 2005, 9(1), 18.
    • (2005) Org. Process Res. Dev. , vol.9 , Issue.1 , pp. 18
    • Synoradzki, L.1    Janczewski, D.2    Wlostowski, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.