Sulfated tin oxide: A reusable and highly efficient heterogeneous catalyst for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives

Synthetic Communications

Volumn 42, Issue 10, 2012, Pages 1509-1520

  Dake, Satish A ^a   Khedkar, Mahesh B ^a   Irmale, Ghanshyam S ^a   Ukalgaonkar, Suhas J ^a   Thorat, Vinod V ^b   Shintre, Suhas A ^b   Pawar, Rajendra P ^b  

^a DNYANOPASAK COLLEGE   (India)

^b DEOGIRI COLLEGE   (India)

Author keywords

2,4,5 triaryl 1H imidazole; Benzil benzoin; Ethanol; Sulfated tin oxide; Water

Indexed keywords

2 (2 METHYL 1H IMIDAZOL 4 YL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3 CHLOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3 NITROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3,4 DIFLUOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (4 CHLORO 3 FLUOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (4 CHLOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (4,5 DIPHENYL 1H IMIDAZOL 2 YL) 6 MEYHOXY PHENOL; 2 BROMO 6 METHOXY 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 2 IODO 6 METHOXY 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 2 METHOXY 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 3 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)BENZONITRILE; 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; ALCOHOL; ALDEHYDE; AMMONIUM ACETATE; IMIDAZOLE DERIVATIVE; TIN OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; SULFATION; SYNTHESIS;

EID: 84857584177     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.541744     Document Type: Article

References (30)

1. (a) Lombardino, J. G.; Wiseman, E. H. Preparation and anti-inflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974, 17, 1182-1188;
2. (b) Sundberg, R. J.; Martin, R. B. Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems. Chem. Rev. 1974, 74, 471-517.
3. Wiglenda, T.; Ott, I.; Kircher, B.; Schumacher, P.; Schuster, D.; Langer, T.; Gust, R. Synthesis and pharmacological evaluation of 1H-imidazoles as ligands for the estrogen receptor and cytotoxic inhibitors of the cyclooxygenase. J. Med. Chem. 2005, 48(20), 6516-6521. (Pubitemid 41429003)
4. Gbadamassi, M.; Barascut, J.; Imbach, J. L.; Gayral, P. Nouveaux anti-parasitaires dans la série du benzimidazole: Synthèse d'hétéroarylamino-2 benzimidazoles et évaluation de leur activitè biologique. Eur. J. Med. Chem. 1988, 23, 225-232.
5. Hazelton, J.; Iddon, B.; Redhouse, A. D.; Suschitzky, H. 2H-benzimidazoles (isobenzimidazoles), part 9: Synthesis and reactions of 4,6-dibromo-2H-benzimidazole-2-spirocyclohexane. Tetrahedron 1995, 51, 5597-5608.
6. Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. T.; Kumar, S.; Green, D.; McKulty, D.; Blumenthal, M.; Heys, J. R.; Landvatter, S. W.; Strikler, J. E.; McLaughlin, M. M.; Siemen, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994, 372, 739-746.
7. Li, H. S.; Rampersaud, A. A.; Zimmerman, K. Synthesis and in vitro evaluation of N[[4-[2-(carboxy)-1-cycloalken-1-yl]phenyl]imidazoles as nonpeptide angiotensin II receptor antagonists. J. Chin. Chem. Soc. 1993, 40, 273-282.
8. (a) Ucucu, U.; Karaburun, N. G.; Isikdag, I. Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives. Farmaco 2001, 56, 285-290; (Pubitemid 32463311)
9. (b) Wolkenberg, S. E.; Wisnosk, 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, 1453-1456. (Pubitemid 38626327)
10. Pozherskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Heterocycles in Life, Society; Wiley: New York, 1997; p. 179.
11. Lombardino, J. G.; Wiseman, E. H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974, 17, 1182.
12. Phillips, A. R.; White, H. L.; Rosen, S. Eur. Pat. Appl. EP 1982, 58, 890
13. Chem. Abstr. 1982, 98, 53894z.
14. Liu, J.; Chem, J.; Zhao, J.; Zhao, Y.; Li, L.; Zhang, H. A Modified procedure for the synthesis of 1-arylimidazoles. Synthesis 2003, 17, 2661-2666. (Pubitemid 37540416)
15. Weinmann, H.; Harre, M.; Koeing, K.; Merten, E.; Tilestam, U. Efficient and environmentally friendly synthesis of 2-amino-imidazole. Tetrahedron Lett. 2002, 43, 593-595. (Pubitemid 34085021)
16. Sarshar, S.; Siev, D.; Mjalli, M. M. Imidazole libraries on solid support. Tetrahedron Lett. 1996, 37, 835-838. (Pubitemid 26047074)
17. Shaabani, A.; Rahmati, A. Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles. J. Mol. Catal. A: Chem. 2006, 249, 246-248.
18. Khodaei, M. M.; Bahrami, K.; Kavianinia, I. p-TSA-catalyzed synthesis of 2,4,5-triarylimidazoles from ammonium heptamolybdate tetrahydrate in TBAI. J Chin. Chem. Soc. 2007, 54, 829-833.
19. Shelke, K. F.; Sapkal, S. B.; Sonar, S. S.; Madje, B. R.; Shingate, B. B.; Shingare, M. S. An efficient synthesis of 2,4,5-triaryl-1H-imidazole derivatives catalyzed by boric acid in aqueous media under ultrasound irradiation. Bull. Korean Chem. Soc. 2009, 30, 1057-1060.
20. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Thomas, D.; 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, 3539-3546. (Pubitemid 40357943)
21. Saimki, A. R.; Arndtsen, B. A. A direct, one-step synthesis of imidazoles from imines and acid chlorides: A palladium-catalyzed multicomponent coupling approach. J. Am. Chem. Soc. 2006, 128, 6050-6051.
22. Zaman, S.; Mitsum, K.; Abell, A. D. Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: Application to amino acid mimetics with a C-terminal imidazole. Org. Lett. 2005, 7, 609-611. (Pubitemid 40353453)
23. Frantz, D. E.; Morency, L.; Soheili, A.; Murry, J. A.; Grabowski, E. J. J.; Tillyer, R. D. Synthesis of substituted imidazoles via organocatalysis. Org. Lett. 2004, 6(5), 843-846. (Pubitemid 38387989)
24. Bilodeu, M. T.; Cunningham, A. M. Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core. J. Org. Chem. 1998, 63, 2800-2801.
25. Shitole, N. V.; Shelke, K. F.; Sonar, S. S.; Sadaphal, S. A.; Shingate, B. B.; Shingare, M. S. L-Proline as an efficient catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles. Bull. Korean Chem. Soc. 2009, 30, 1963-1966.
26. 2O. Tetrahedron Lett. 2008, 49, 2216-2220.
27. Matsuhashi, H.; Miyazaki, H.; Kawamura, Y.; Nakamura, H.; Arata, K. Preparation of a solid superacid of sulfated tin oxide with acidity higher than that of sulfated zirconia and its applications to aldol condensation and benzoylation. Chem. Mater. 2001, 13, 3038-3042. (Pubitemid 33121309)
28. (a) Parveen, A.; Ahmed, M. R. S.; Shaikh, K. A.; Deshmukh, S. P.; Pawar, R. P. Efficient synthesis of 2,4,5-triaryl substituted imidazoles under solvent-free conditions at room temperature. Arkivoc 2007, 16, 12-18;
29. (b) Nalage, S. V.; Kalyankar, M. B.; Patil, V. S.; Bhosale, S. V.; Deshmukh, S. U.; Pawar, R. P. An efficient noncatalytic protocol for the synthesis of trisubstituted imidazole in polyethylene glycol using microwaves. Open Catal. J. 2010, 3, 50-53.
30. Sarda, S. R.; Puri, V. A.; Rode, A. B.; Dalawe, T. N.; Jadhav, W. N.; Pawar, R. P. Sulfated tin oxides: A suitable reagent for synthesis of 2,4-diphenyl-4,6,7,8-tetrahydrochromen-5-one. Arkivoc 2007, 16, 246-251.