β-Cyclodextrin-catalyzed mild aromatization of hantzsch 1,4-dihydropyridines with o-iodoxybenzoic acid in water/acetone

Synthetic Communications

Volumn 39, Issue 19, 2009, Pages 3521-3526

  Chen, Jiang Min ^a   Zeng, Xiao Mei ^a,b  

^a JIAXING UNIVERSITY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

cyclodextrin; Aromatization; Hantzsh 1,4 dihydropyridines; O iodoxybenzoic acid (IBX); Pyridine derivatives

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ACETONE; BENZOIC ACID DERIVATIVE; BETA CYCLODEXTRIN; WATER;

AROMATIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RECYCLING;

EID: 70349217114     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902788133     Document Type: Article

References (33)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1988.
2. Matlack AS Introduction to Green Chemistry; Marcel Dekker Inc.: New York, 2001
3. Lancester, M. Green Chemistry: An Introductory Text; Royal Society of Chemistry: Cambridge, 2002
4. Clark, J. H.; Macquarrie, D. Handbook of Green Chemistry and Technology; Blackwell Publishers: Oxford, 2002.
5. Breslow, R.; Dong, S. D. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 1998, 98, 1997-2011
6. Surendra, K.; Srilakshmi Krishnaveni, N.; Arjun Reddy, M.; Nageswar, Y. V. D.; Rama Rao, K. Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in water= acetone mixture in the presence of b-cyclodextrin. J. Org. Chem. 2003, 68, 2058-2059 (Pubitemid 36504876)
7. Surendra, K.; Krishnaveni, N. S.; Mahesh, A.; Rao, K. R. Supramolecular catalysis of Strecker reaction in water under neutral conditions in the presence of b-cyclodextrin. J. Org. Chem. 2006, 71, 2532-2534
8. b-Cyclodextrin-Catalyzed Aromatization 3525
9. Kumar, V. P.; Reddy, V. P.; Sridhar, R.; Srinivas, B.; Narender, M.; Rao, K. R. Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water. J. Org. Chem. 2008, 73, 1646-1648.
10. Triggle, D. J. In Comprehensive Medicinal Chemistry; J. C. Emmett (Ed.), Pergamon: Oxford, 1990, vol.3, chapter 14.1.
11. Böcker, R. H.; Guengerich, F. P. Oxidation of 4-aryl-and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyri-dines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. J. Med. Chem. 1986, 29, 1596-1603
12. Guengerich, F. P.; Brian, W. R.; Iwasaki, M.; Sari, M.-A.; Bäärnhielm, C.; Berntsson, P. Oxidation of dihydropyridine calcium channel blockers and analogs by human liver cytochrome P-450 IIIA4. J. Med. Chem. 1991, 34, 1838-1844.
13. Yin, X. H. Advances in synthesis and aromatization of Hantzsch 1,4-dihy-dropyridine derivatives. Chemistry 2003, 66 (w092), 1-11
14. Eynde, J. J. V.; Mayence, A. Synthesis and aromatization of Hantzsch 1,4-dihydropyridines under microwave irradiation: An overview. Molecules 2003, 8, 381-391
15. Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Fatima, N.; Yadav, J. S. Zr(NO3)4: A versatile oxidizing agent for aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines. Synthesis 2003, 1267-1271
16. Nakamichi, N.; Kawashita, Y.; Hayashi, M. Activated carbon-promoted oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines using molecular oxygen. Synthesis 2004, 1015-1020
17. Han B., Liu Q., Liu Z. G., Mu R. Z., Zhang W., Liu Z. L., Yu W., A metal-free catalytic aerobic aromatization of Hantzsch 14-dihydropyridines by n-hydroxyphthalimide. Synlett 2005, 2333-2334
18. Xia JJ, Wang GW, One-pot synthesis and aromatization of 14-dihydro-pyridines in refluxing water. Synthesis 2005, 2379-2383
19. Yadav, I. J. S.; Reddy, B. V. S.; Basak, A. K.; Baishya, G.; Venkat Narsaiah, A. Iodoxyben-zoic acid (IBX): An efficient and novel oxidizing agent for the aromatization of 1,4-dihydropyridines. Synthesis 2006, 451-454
20. Bagley M. C., Lubinu M. C., Microwave-assisted oxidative aromatization of Hantzsch 14-dihydro-pyridines using manganese dioxide. Synthesis 2006, 1283-1288
21. Han, B.; Liu, Z. G.; Liu, Q.; Yang, L.; Liu, Z. L.; Yu, W. An efficient aerobic oxida-tive aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines. Tetrahedron 2006, 62, 2492-2496
22. Matern, A. I.; Charushin, V. N.; Chupakhin, O. N. Progress in the studies of oxidation of dihydropyr-idines and their analogues. Uspekhi Khimii 2007, 76, 27-45.
23. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997
24. Wirth T., Hirt U. H., Hypervalent iodine compounds: Recent advances in synthetic applications. Synthesis 1999, 1271-1287
25. Zhdankin, V. V.; Stang, P. J. Recent developments in the chemistry of polyvalent iodine compounds. Chem. Rev. 2002, 102, 2523-2584
26. Stang, P. J. Polyvalent iodine in organic chemistry. J. Org. Chem. 2003, 68, 2997-3008
27. Kumar, I. 2-Iodoxybenzoic acid (IBX): A versatile reagent. Synlett. 2005, 1488-1489.
28. Mulbaier, M.; Giannis, A. The synthesis and oxidative properties of polymer-supported IBX. Angew. Chem., Int. Ed. 2001, 40, 4393-4394
29. Moore, J. D.; Finney, S. N. A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX). Org. Lett. 2002, 4, 3001-3003;
30. Ladziata, U.; Zhdankin, V. V. Hypervalent iodine(V) reagents in organic synthesis. Arkivoc 2006, 9, 26-58.
31. Li, F. Q.; Zeng, X. M.; Chen, J. M. Poly{[4-(hydroxy)(tosyloxy)iodo]styr- ene}-promoted aromatisation of Hantzsch 1,4-dihydropyridines. J. Chem. Res., Synop. 2007, 619-620.
32. Frigerio, M.; Santagostino, M.; Sputore, S. A user-friendly entry to 2-iodox-ybenzoic acid (IBX). J. Org. Chem. 1999, 64, 4537-4538.
33. Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. Hantzsch-type dihydropyridine hypotensive agents. J. Med. Chem. 1974, 17, 956.