Facile method for one-step synthesis of 2,4,5-triarylimidazoles under catalyst-free, solvent-free, and microwave-irradiation conditions

Synthetic Communications

Volumn 40, Issue 8, 2010, Pages 1134-1141

  Zhou, Jian Feng ^a,b   Gong, Gui Xia ^b   Sun, Xiao Jun ^a   Zhu, Yu Lan ^a  

^a HUAIYIN NORMAL UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

Aromatic aldehyde; Benzil; Catalyst free; Microwave irradiation; Solvent free; Triarylimidazole

Indexed keywords

2,4,5 TRIARYLIMIDAZOLE DERIVATIVE; ALDEHYDE; AMMONIUM ACETATE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; MICROWAVE IRRADIATION; POLYMERIZATION; REACTION TIME; SYNTHESIS;

EID: 77949349932     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903043025     Document Type: Article

References (31)

1. Liebl, R.; Handte, R.; Mildenberger, H.; Bauer, K.; Bieringer, H. Preparation of 1-phenyl-2-imidazolidinones and 2-imidazolidinethiones as herbicides. Ger. Offen. 3, 604,042, Aug. 13, 1987;
2. Chem. Abstr. 1988, 108(1), 6018g.
3. Pozherskii, A. F.; Soldatenkov, A. T.; Katritzky, A. Y. Heterocycles in Life and Society; Wiley: New York, 1997; pp. 179-180.
4. Lombardino, J. G.; Wiseman, E. H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974, 17, 1182-1188.
5. Phillips, A. P.; White, H. L.; Rosen, S. Antithrombotic triphenylimidazole. Eur. Patent Appl. EP 58,890, Sep. 1, 1982;
6. Chem. Abstr. 1983, 98(7), 53894z.
7. (a) Satoru, I. Imidazoles derivative for chemiluminescence microanalysis. Jpn. Kokkai Tokyo Koho JP 01,117,867, May 10, 1989;
8. Chem. Abstr. 1989, 111(23), 214482t;
9. (b) Sensui, H.; Ichikawa, J.; Sato, S. Photosensitive composition containing triphenylimida-zole dimer. Jpn. Kokkai Tokyo Koho JP 62,94,841, Mar. 4, 1987;
10. Chem. Abstr. 1987, 107(20), 187436q.
11. Chang, L. L.; Sidler, K. L.; Cascieri, M. A.; de Laszlo, S.; Koch, G.; Li, B.; MacCoss, M.; Mantlo, N.; O'Keefe, S.; Pang, M.; Rolando, A.; Hagmann, W. K. Substituted imidazoles as glucagon receptor antagonists. Bioorg. Med. Chem. Lett. 2001, 11, 2549-2553.
12. s.) Gallagher, T. H.; 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, 1171-1176.
13. Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Rees, E. F. V. Scriven (Eds.); Pergamon: New York, 1996; vol.3, p. 77.
14. 4. Synth. Commun. 2006, 36, 2991-3000.
15. Balalaie, S.; Arabanian, A.; Hashtroudi, M. S. Zeolite HY and silica gel as new and efficient heterogenous catalysts for the synthesis of triarylimidazoles under microwave irradiation. Monat. Chem. 2000, 131, 945-948.
16. Sangshetti, J.; Kokare, N.; Kotharkar, A.; Shinde, D. Sodium bisulfite as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil or benzoin and aromatic aldehydes. Monat. Chem. 2008, 139, 125-127.
17. Mohammed, A.; Lokare, N.; Sangshetti, J.; Shinde, D. Sulphanilic acid-catalyzed facile one-pot synthesis of 2,4,5-triarylimidazoles from benzil=benzoin and aromatic aldehydes. J. Kor. Chem. Soc. 2007, 51, 418-422.
18. Kidwai, M.; Mothsra, P.; Bansal, V.; Goyal, R. Efficient elemental iodine catalyzed one-pot synthesis of 2,4,5-triarylimidazoles. Monat. Chem. 2006, 137, 1189-1194.
19. 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, 3539-3546.
20. Ahmad, S.; Maleki, A.; Benham, M. Tandem oxidation process using ceric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions. Synth. Commun. 2009, 39, 102-110.
21. (a) Davidson, D.; Weiss, M.; Jelling, M. The action of ammonia on benzil. J. Org. Chem., 1937, 2, 319-327;
22. (b) Whiten, D. M.; Sonnenberg, J. Infrared spectra of arylimidazoles and arylisoimidazoles. J. Org. Chem. 1964, 29, 1926-1930.
23. Zhang, E. J.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. The Curtin-Hammett principle: Stereoselective radical additions to alkenes. Teterahedron Lett. 1996, 37, 351-354.
24. Zhou, J. F.; Song, Y. Z.; Yang, Y. L.; Zhu, Y. L.; Tu, S. J. One-step synthesis of 2-aryl-4,5-diphenylimidazoles under microwave irradiation. Synth. Commun. 2005, 35, 1369-1373.
25. Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
26. Ding, D. R.; Li, X.; Wang, X.; Du, Y. L.; Shen, J. K. Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2-aminoacetopheinones. Tetrahderon Lett. 2006, 47, 6997-6999.
27. Loupy, A.; Petti, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using focused microwaves. Synthesis 1998, 1213-1234.
28. Motiwala, H. F.; Kumar, R.; Chakraborti, A. K. Microwave-accelerated solvent-and catalyst-free synthesis of 4-aminoaryl=alkyl-7-chloroquinolines and 2-aminoaryl=alkyl-benzothiazoles. Aust. J. Chem. 2007, 60, 369-374.
29. Jeselnik, M.; Varma, R. S.; Polanc, S.; Kocevar, M. Catalyst-free reactions under solvent-free conditions: Microwave-assisted synthesis of heterocyclic hydrazones below the melting points of neat reactants. Chem. Commun. 2001, 21, 1716-1717.
30. Mu, X. J.; Lei, M. Y.; Zou, J. P.; Zhang W. Microwave-assisted free solvent-and catalyst-free Kabachnik-Fields reactions for a-amino phosphonates. Tetrahedron Lett. 2006, 47, 1125-1127.
31. Zhou, J. F.; Gong, G. X.; Zhi, S. J.; Duan, X. L. Microwave-assisted catalyst-free and solvent-free method for the synthesis of quinoxalines. Synth. Commun. 2009, 39, 3743-3754.