An Efficient Synthesis of Tri- and Tetrasubstituted Imidazoles from Benzils Using Functionalized Chitosan as Biodegradable Solid Acid Catalyst

Industrial and Engineering Chemistry Research

Volumn 54, Issue 26, 2015, Pages 6611-6618

  Khan, Kulsum ^a   Siddiqui, Zeba N ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHITIN; CHITOSAN; MICROWAVE IRRADIATION; PLANTS (BOTANY);

COMPONENT SYNTHESIS; EFFICIENT CATALYSTS; EFFICIENT SYNTHESIS; ENVIRONMENTALLY BENIGN; HAZARDOUS SOLVENTS; HETEROGENEOUS ACIDIC CATALYSTS; IMIDAZOLE DERIVATIVES; SOLID ACID CATALYSTS;

PHOTOSENSITIZERS;

EID: 84936162088     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/acs.iecr.5b00511     Document Type: Article

References (56)

1. D'Souza, D. M.; Mueller, T. J. J. Multi-component syntheses of heterocycles by transition metal catalysis Chem. Soc. Rev. 2007, 36, 1095
2. Kappe, C. O. Controlled microwave heating in modern organic synthesis Angew. Chem., Int. Ed. 2004, 43, 6250
3. Bailey, D. C.; Langer, S. H. Immobilized transition-metal carbonyls and related catalysts Chem. Rev. 1981, 81, 109
4. Rinaudo, M. Chitin and chitosan: Properties and applications Prog. Polym. Sci. 2006, 31, 603-632
5. Dash, M.; Chiellini, F.; Ottenbrite, R. M.; Chiellini, E. Chitosan-A versatile semi-synthetic polymer in biomedical applications Prog. Polym. Sci. 2011, 36, 981
6. Macquarrie, D. J.; Hardy, J. J. E. Applications of functionalized chitosan in catalysis Ind. Eng. Chem. Res. 2005, 44, 8499
7. Xiao, L. F.; Li, F. W.; Xia, C. G. An easily recoverable and efficient natural biopolymer-supported zinc chloride catalyst system for the chemical fixation of carbon dioxide to cyclic carbonate Appl. Catal., A 2005, 279, 125
8. Huai-min, G.; Xian-su, C. Study of cobalt(II)-chitosan coordination polymer and its catalytic activity and selectivity for vinyl monomer polymerization Polym. Adv. Technol. 2004, 15, 89
9. Quignard, F.; Choplin, A.; Domard, A. Chitosan: A natural polymeric support of catalysts for the synthesis of fine chemicals Langmuir 2000, 16, 9106
10. Hardy, J. J. E.; Hubert, S.; Macquarrie, D. J.; Wilson, A. J. Chitosan-based heterogeneous catalysts for Suzuki and Heck reactions Green Chem. 2004, 6, 53
11. Guibal, E. Heterogeneous catalysis on chitosan-based materials: A review Prog. Polym. Sci. 2005, 30, 71
12. Mohammadi, R.; Kassaee, M. Z. Sulfochitosan encapsulated nano-Fe3O4 as an efficient and reusable magnetic catalyst for green synthesis of 2-amino-4 H -chromen-4-yl phosphonates J. Mol. Catal. A: Chem. 2013, 380, 152
13. Reddy, B. V. S.; Venkateswarlu, A.; Reddy, G. N.; Reddy, Y. V. R. Chitosan-SO3H: an efficient, biodegradable, and recyclable solid acid for the synthesis of quinoline derivatives via Friedländer annulation Tetrahedron Lett. 2013, 54, 5767
14. Gallagher, T. F.; Fier-Thompson, S. M.; Garigipati, R. S.; Sorenson, M. E.; Smietana, J. M.; Lee, D.; Bender, P. E.; Lee, J. C.; Laydon, J. T.; Griswold, D. E.; Chabot-Fletcher, M. C.; Breton, J. J.; Adams, J. L. 2,4,5-Triarylimidazole inhibitors of IL-1 biosynthesis Bioorg. Med. Chem. Lett. 1995, 5, 1171
15. Antolini, M.; Bozzoli, A.; Ghiron, C.; Kennedy, G.; Rossi, T.; Ursini, A. Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1 H -imidazole as potential antibacterial agents Bioorg. Med. Chem. Lett. 1999, 9, 1023
16. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Pyrimidinylimidazole inhibitors of CSBP/p38 kinase demonstrating decreased inhibition of hepatic cytochrome p450 enzymes Bioorg. Med. Chem. Lett. 1998, 8, 3111
17. de Laszlo, S. E.; Hacker, C.; Li, B.; Kim, D.; MacCoss, M.; Mantlo, N.; Pivnichny, J. V.; Colwell, L.; Koch, G. E.; Cascieri, M. A.; Hagmann, W. K. Potent, orally absorbed glucagon receptor antagonists Bioorg. Med. Chem. Lett. 1999, 9, 641
18. Laufer, S.; Hauser, D.; Stegmiller, T.; Bracht, C.; Ruff, K.; Schattel, V.; Albrecht, W.; Koch, P. Tri- and tetrasubstituted imidazoles as p38α mitogen-activated protein kinase inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 6671
19. Sarshar, S.; Zhang, C.; Moran, E. J.; Krane, S.; Rodarte, J. C.; Benbatoul, K. D.; Dixon, R.; Mjallik, A. M. M. 2,4,5-trisubstituted imidazoles: Novel nontoxic modulators of p-glycoprotein mediated multidrug resistance. Part 1 Bioorg. Med. Chem. Lett. 2000, 10, 2599
20. Deprez, P.; Mandine, E.; Vermond, A.; Lesuisse, D. Imidazole-based ligands of the Src SH2 protein Bioorg. Med. Chem. Lett. 2002, 12, 1287
21. 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. Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation J. Med. Chem. 2002, 45, 1697
22. Weinstein, D. S.; Liu, W.; Ngu, K.; Langevine, C.; Combs, D. W.; Zhuang, S.; Chen, C.; Madsen, C. S.; Harper, T. W.; Robl, J. A. Discovery of selective imidazole-based inhibitors of mammalian 15-lipoxygenase: Highly potent against human enzyme within a cellular environment Bioorg. Med. Chem. Lett. 2007, 17, 5115
23. Lange, J. H. M.; Stuivenberg, H. H. V.; Coolen, H. K. A. C.; Adolfs, T. J. P.; McCreary, A. C.; Keizer, H. G.; Wals, H. C.; Veerman, W.; Borst, A. J. M.; Looff, W. de; Verveer, P. C.; Kruse, C. G. Bioisosteric replacements of the pyrazole moiety of rimonabant: synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antagonists J. Med. Chem. 2005, 48, 1823
24. 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. The identification of potent and selective imidazole-based inhibitors of B-Raf kinase Bioorg. Med. Chem. Lett. 2006, 16, 378
25. DeTitta, G. T.; Edmonds, J. W.; Stallings, W.; Donohue, J. Molecular structure of biotin. results of two independent crystal structure investigations J. Am. Chem. Soc. 1976, 98, 1920
26. Bonnet, J. J.; Ibers, J. A. Structure of histamine J. Am. Chem. Soc. 1973, 95, 4829
27. Li, S.; Hong, M. Protonation, tautomerization, and rotameric structure of histidine: A Comprehensive study by magic-angle-spinning solid-state NMR J. Am. Chem. Soc. 2011, 133, 1534
28. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis Chem. Rev. 2002, 102, 3667
29. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Reactivity of ionic liquids Tetrahedron 2007, 63, 2363
30. Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. Highly efficient, four-component one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts J. Mol. Catal. A: Chem. 2007, 263, 112
31. Balalaie, S.; Arabanian, A. One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation Green Chem. 2000, 2, 274
32. Mohammed, A.; Kokare, N.; Sangshetti, J.; Shinde, D. Sulphanilic acid catalyzed facile one-pot synthesis of 2,4,5-triarylimidazoles from benzil/benzoin and aromatic aldehydes J. Korean Chem. Soc. 2007, 51, 418
33. Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R. K.; Ethayathulla, A. S.; Dey, S.; Singh, T. P. One-pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst J. Mol. Catal. A: Chem. 2007, 265, 177
34. Siddiqui, S.; Narkhede, U.; Palimkar, S.; Daniel, T.; Lahoti, R.; Srinivasan, K. Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triaryl imidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketone Tetrahedron 2005, 61, 3539
35. Karimi, A. R.; Alimohammadi, Z.; Azizian, J.; Mohammadi, A. A.; Mohammadizadeh, M. R. Solvent-free synthesis of tetrasubstituted imidazoles on silica gel/NaHSO4 support Catal. Commun. 2006, 7, 728
36. Kantevari, S.; Vuppalapati, S. V. N.; Biradar, D. O.; Nagarapu, L. Highly efficient, one-pot, solvent-free synthesis of tetrasubstituted imidazoles using HClO4-SiO2 as novel heterogeneous catalyst J. Mol. Catal. A: Chem. 2007, 266, 109
37. Heravi, M. M.; Derikv, F.; Haghighi, M. Highly efficient, four component, one-pot synthesis of tetrasubstituted imidazoles using a catalytic amount of FeCl3.6H2O Monatsh. Chem. 2008, 139, 31
38. Sadeghi, B.; Mirjalili, B. B. F.; Hashemi, M. M. BF3.SiO2: An efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles Tetrahedron Lett. 2008, 49, 2575
39. Usyatinsky, A. Y.; Khmelnitsky, Y. L. Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions Tetrahedron Lett. 2000, 41, 5031
40. Sharma, S. D.; Hazarika, P.; Konwar, D. An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O Tetrahedron Lett. 2008, 49, 2216
41. Lipshutz, B. H.; Morey, M. C. An approach to the cyclopeptide alkaloids (phencyclopeptines) via heterocyclic diamide/dipeptide equivalents. Preparation and N -alkylation studies of 2,4(5)-disubstituted imidazoles J. Org. Chem. 1983, 48, 3745
42. Mohammadizadeh, M. R.; Hasaninejad, A.; Bahramzadeh, M. Trifluoroacetic acid as an efficient catalyst for one-pot, four-component synthesis of 1,2,4,5-tetrasubstituted imidazoles under microwave-assisted, solvent-free conditions Synth. Commun. 2009, 39, 3232
43. 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, 10155
44. Teimouri, A.; Chermahini, A. N. 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. 2011, 346, 39
45. Zarnegar, Z.; Safari, J. Fe3O4@chitosan nanoparticles: A valuable heterogeneous nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles RSC Adv. 2014, 4, 20932
46. Zhou, J. F.; Song, Y. Z.; Zhu, Y. L.; Tu, S. J. One-step synthesis of 2-aryl-4,5-diphenylimidazoles under microwave irradiation Synth. Commun. 2005, 35, 1369
47. Siddiqui, Z. N.; Khan, K.; Ahmed, N. Nano fibrous silica sulphuric acid as an efficient catalyst for the synthesis of β-enaminone Catal. Lett. 2014, 144, 623
48. Siddiqui, Z. N.; Khan, K. Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions New J. Chem. 2013, 37, 1595
49. Siddiqui, Z. N.; Khan, K. [Et3NH][HSO4]-catalyzed efficient, eco-friendly, and sustainable synthesis of quinoline derivatives via knoevenagel condensation ACS Sustainable Chem. Eng. 2014, 2, 1187
50. Ilczyszyn, M. M.; Ilczyszyn, M. Raman, infrared and 13C NMR studies on betaine-sulfamic acid (2:1) crystal and its hydrogen bonds J. Raman Spectrosc. 2003, 34, 693
51. Ghiaci, M.; Dorostkar, N.; Martínez-Huerta, M. V.; Fierro, J. L.G.; Moshiri, P. Synthesis and characterization of gold nanoparticles supported on thiol functionalized chitosan for solvent-free oxidation of cyclohexene with molecular oxygen J. Mol. Catal. A: Chem. 2013, 379, 340
52. Sait, H.; Tabeta, R. High-resolution solid-state 13C NMR study of chitosan and its salts with acids: Conformational characterization of polymorphs and helical structures as viewed from the conformation-dependent 13C chemical shifts Macromolecules 1987, 20, 2424
53. Kidwai, M.; Saxena, S.; Ruby; Rastogi, S. An efficient synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1 H -imidazoles Bull. Korean Chem. Soc. 2005, 26, 2051
54. Safari, J.; Khalili, S. D.; Rezaei, M.; Banitab, S. H.; Meshkani, F. Nanocrystalline magnesium oxide: a novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives Monatsh. Chem. 2010, 141, 1339
55. Siddiqui, S. A.; Narkhede, U. C.; Pallmkar, 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 α-hydroxyketone Tetrahedron 2005, 61, 3539
56. Hasaninejad, A.; Zare, A.; Shekouhy, M.; Rad, J. A. Catalyst-free one-pot four component synthesis of polysubstituted imidazoles in neutral ionic liquid 1-butyl-3-methylimidazolium bromide J. Comb. Chem. 2010, 12, 844