Tandem oxidation process using ceric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions

Synthetic Communications

Volumn 39, Issue 1, 2009, Pages 102-110

  Shaabani, Ahmad ^a   Maleki, Ali ^a   Behnam, Maryam ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Aerobic oxidation; Ceric ammonium nitrate (CAN); Tandem oxidation process (TOP); Three component reaction; Trisubstituted imidazole

Indexed keywords

2 (3 CHLOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3 NITROPHENYL) 4,5 DIPHENYLIMIDAZOLE; 2 (4 BROMOPHENYL) 4,5 DIPHENYLIMIDAZOLE; 2 (4 METHOXYPHENYL) 4,5 DIPHENYLIMIDAZOLE; 2 (4 METHYLPHENYL) 4,5 DIPHENYLIMIDAZOLE; 2 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 2,4,5 TRIPHENYLIMIDAZOLE; 4,5 BIS(4 METHOXYPHENYL) 2 4 TOLYL 1H IMIDAZOLE; 4,5 BIS(4 METHOXYPHENYL) 2 PHENYL 1H IMIDAZOLE; ALCOHOL; ALDEHYDE DERIVATIVE; AMMONIUM ACETATE; AMMONIUM NITRATE; BENZALDEHYDE; CERIC AMMONIUM NITRATE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; OXIDATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 57449091360     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802369661     Document Type: Article

References (27)

1. Dembitsky, V. M.; Gloriozova, T. A.; Poroikov, V. V. Novel antitumor agents: Marine sponge alkaloids, their synthetic analogs and derivatives. Mini-Rev. Med. Chem. 2005, 5, 319.
2. Vallee, B. L.; Auld, D. S. Zinc coordination, function, and structure of zinc enzymes and other proteins. Biochemistry 1990, 29, 5647.
3. Liu, J.; Zhao, Y.; Zhou, Y.; Li, L.; Zhang, T. Y.; Zhang, H. Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air. Org. Biomol. Chem. 2003, 1, 3227.
4. Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Ress, E. F. V. Scriven, (Eds.); Pergamon Press: Oxford, 1996; vol. 3, p. 77.
5. Adams, J. L.; Lee, D. Recent progress towards the identification of selective inhibitors of serine/threonine protein kinases.Curr. Opin. Drug Discov. Dev. 1999, 2, 96.
6. Khanna, I. K.; Yu, Y.; Huff, R. M.; Weier, R. M.; Xu, X. D.; Koszyk, F. J.; Collins, P. W.; Cogburn, J. N.; Isakson, P. C.; Kobolt, C. M.; Masferrer, J. L.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Yuan, J.; Yang D.; Zhang, Y. Y. Selective cyclooxygenase-2 inhibitors: Heteroaryl modified 1, 2-diarylimidazoles are potent, orally active antiinflammatory agents. J. Med. Chem. 2000, 43, 3168.
7. Liebl, R.; Handte, R.; Mildenberger, H.; Bauer, K.; Bieringer, H. Procedimiento para la sintesis de 2-imidazolidinonas, poli-sustituidas. Ger. Offen DE. 3,604,042; 1987. Chem. Abstr. 1987; 108, 6018g.
8. Pozherskii, A. F.; Soldatenkov, A. T.; Kareizky, A. R. Heterocycles in Life, Society; Wiley: New York, 1997; p. 179.
9. 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.
10. Lombandine, J. G.; Wiseman, E. H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974, 17, 1182.
11. Baldwin, J. J.; Remy, D. C.; Claremon, D. A. Certain imidazole compounds as transglutaminase inhibitors. US Patent 4,968,713; 2001.
12. Sarshar, S.; Siev, D.; Mjalli, A. M. M. Imidazole libraries on solid support. Tetrahedron Lett. 1996, 37, 835.
13. 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.
14. Shaabani, A.; Rahmati, A. Silica sulfuric acid as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles. J. Mol. Catal. A 2006, 249, 246, and references cited therein.
15. Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Tandem oxidation processes using manganese dioxide: Discovery, applications, and current studies. Acc. Chem. Res. 2005, 38, 851.
16. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes. Chem. Commun. 2003, 2286.
17. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org. Biomol. Chem. 2004, 2, 788.
18. Mueller, J. A.; Goller, C. P.; Sigman, M. S. Elucidating the significance of β-hydride elimination and the dynamic role of acid/base chemistry in a palladium-catalyzed aerobic oxidation of alcohols. J. Am. Chem. Soc. 2004, 126, 9724.
19. Robinson, R. S.; Taylor, R. J. K. Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation. Synlett 2005, 1003.
20. Shaabani, A.; Maleki, A. Green and efficient synthesis of quinoxaline derivatives via ceric ammonium nitrate promoted and in situ aerobic oxidation of α-hydroxy ketones and α-keto oximes in aqueous media. Chem. Pharm. Bull. 2008, 56, 79.
21. Shaabani, A.; Maleki, A.; Moghimi-Rad, J.; Soleimani, E. Cellulose sulfuric acid catalyzed one-pot three-component synthesis of imidazoazines. Chem. Pharm. Bull. 2007, 55, 957.
22. Shaabani, A.; Maleki, A. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of α-amino nitriles. Appl. Catal. A: Gen. 2007, 331, 149.
23. Shaabani, A.; Rahmati, A. Aerobic oxidation of alkyl arenes using a combination of N-hydroxy phthalimide and recyclable cobalt(II) tetrasulfophthalocyanine supported on silica. Catal. Commun. 2008, 9, 1692.
24. Shaabani, A.; Farhangi, E.; Rahmati, A. Aerobic oxidation of alkyl arenes and alcohols using cobalt(II) phthalocyanine as a catalyst in 1-butyl-3-methyl-imidazolium bromide. Appl. Catal. A: Gen. 2008, 338, 14.
25. Kim, S. S.; Jung, H. C. An efficient aerobic oxidation of alcohols to aldehydes and ketones with TEMPO/ceric ammonium nitrate as catalysts. Synthesis, 2003, 2135.
26. Nair, V.; Suja, T. D.; Mohanan, K. A convenient synthesis of 2,2-diarylcyclobutanones by cerium(IV) ammonium nitrate (CAN) mediated oxidation of methylenecyclopropanes (MCPs). Synthesis 2006, 2531.
27. Nair, V.; Deepthi, A. Cerium(IV) ammonium nitrate-a versatile single-electron oxidant. Chem. Rev. 2007, 107, 1862.