Zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] as an efficient lewis acid-surfactant combined catalyst for the synthesis of quinoxaline derivatives in aqueous media

Synthetic Communications

Volumn 39, Issue 4, 2009, Pages 569-579

  Hasaninejad, Alireza ^a   Zare, Abdolkarim ^b   Zolfigol, Mohammad Ali ^c   Shekouhy, Mohsen ^a  

^a PERSIAN GULF UNIVERSITY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

^c BU ALI SINA UNIVERSITY   (Iran)

Author keywords

1,2 Diamine; 1,2 diketone; Green chemistry; H2O; Quinoxaline; Zirconium tetrakis(dodecyl sulfate)

Indexed keywords

2,3 DIPHENYLBENZO[G]QUINOXALINE; 2,3 DIPHENYLQUINOXALINE; 9,10 DIMETHYLACENAPHTHO[1,2 B]QUINOXALINE; DIAMINE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; WATER; ZIRCONIUM DERIVATIVE; ZIRCONIUM TETRAKIS(DODECYL SULFATE);

ARTICLE; CATALYST; DRUG SYNTHESIS; POLYMERIZATION; ROOM TEMPERATURE;

EID: 61849138988     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802406737     Document Type: Article

References (44)

1. (a) Grieco, P. A. Organic Synthesis in Water; Blackie Academic and Professional: London, 1998;
2. (b) Anastas, P. T.; Williamson, T. C. (Eds). Green Chemistry (ACS Symposium Series 626), American Chemical Society: Washington, DC, 1996;
3. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997;
4. (d) Anastas, P.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press, Oxford, 1998;
5. (e) Li, C.-J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update. Chem. Rev. 2005, 105, 3095-3165.
6. (a) Kobayashi, S.; Manabe, K.; Nagayama, S. Modern Carbonyl Chemistry; J. Otera (Ed.); Wiley-VCH: Weinheim, 2000;
7. (b) Manabe, K.; Mori, Y.; Wakabayashi, T.; Nagayama, S.; Kobayashi, S. Organic synthesis inside particles in water: Lewis acid-surfactant combined catalysts for organic reactions in water using colloidal dispersions as reaction media. J. Am. Chem. Soc. 2000, 122, 7202-7207;
8. (c) Kobayashi, S.; Nagayama, S.; Busujima, T. Lewis acid catalysts stable in water: Correlation between catalytic activity in water and hydrolysis constants and exchange rate constants for substitution of inner-sphere water ligands. J. Am. Chem. Soc. 1998, 120, 8287-8288.
9. (a) Mnabe, K.; Aoyama, N.; Kobayashi, S. Friedel-Crafts-type Conjugate addition of indoles using a Lewis acid-surfactant combined catalyst in water. Adv. Synth. Catal. 2001, 343, 174-176;
10. (b) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Michael reactions in water using Lewis acid-surfactant combined catalysts. Tetrahedron Lett. 2000, 41, 3107-3111.
11. 2O in water. Chem. Commun. 2005, 789-791;
12. 2O as an efficient Lewis acid-surfactant combined catalyst for organic reactions in water: Efficient conversion of epoxides to thiiranes and to amino alcohols at room temperature. J. Mol. Cat. A: Chem. 2007, 274, 109-115.
13. Zolfigol, M. A.; Salehi, P.; Ghaderi, A.; Shiri, M.; Tanbakouchian, Z. An eco-friendly procedure for the synthesis of polysubstituted quinolines under aqueous media. J. Mol. Cat. A: Chem. 2006, 259, 253-258.
14. (a) Brock, E. D.; Lewis, D. M.; Yousaf, T. I.; Harper, H. H. Reactive dyes and their use. WO 9951688, 1999;
15. (b) Thomas, K. R.; Marappan, V.; Jiann, T. L.; Chang-Hao, C.; Yu-ai, T. Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials. Chem. Mater. 2005, 17, 1860-1866;
16. (c) Dailey, S.; Feast, J. W.; Peace, R. J.; Saga, R. C.; Till, S.; Wood, E. L. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications. J. Mater. Chem. 2001, 11, 2238-2243;
17. (d) Jonathan, L. S.; Hiromitsu, M.; Toshisha, M.; Vincent, M. L.; Hiroyuki, F. Quinoxaline-oligopyrroles: Improved pyrrole-based anion receptors. Chem. Commun. 2002, 862-863.
18. Hui, X.; Desrivot, J.; Bories, C.; Loiseau, P. M.; Franck, X.; Hocquemiller, R.; Figadere, B. Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines. Bioorg. Med. Chem. Lett. 2006, 16, 815-820;
19. (b) Dell, A.; William, D. H.; Morris, H. R.; Smith, G. A.; Feeney, J. Roberts, G. C. K. Structure revision of the antibiotic echinomycin. J. Am. Chem. Soc. 1975, 97, 2497-2502;
20. (c) Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Synthesis of new quinoxaline-2-carboxylate1, 4-dioxide derivatives as anti-Mycobacterium tuberculosis agents. J. Med. Chem. 2005, 48, 2019-2025;
21. (d) Aguirre, G.; Cerecetto, H.; DiMaio, R.; Gonzales, M.; Alfaro, M. E. M. A.; Jaso, A.; Zarranz, B.; Ortega, M. A.; Aldana, I.; Monge-Vega, A. Quinoxaline N,N′-dioxide derivatives and related compounds as growth in hibitors of Trypanosoma cruzi: Structure-activity relationships. Bioorg. Med. Chem. Lett. 2004, 14, 3835-3839;
22. 2/M cell cycle arrest and apoptosis in human colon cancer cells. Cancer Chemoth. Pharm. 2005, 55, 369-378;
23. (f) Toshima, K.; Ozawa, T.; Kimura, T.; Matsumara, S. The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids. Bioorg. Med. Chem. Lett. 2004, 14, 2777-2779.
24. 3: A novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines. Org. Lett. 2005, 7, 2169-2172;
25. (b) Xekoukoulotakis, N. P.; Hadjiantonious-Maroulis, C. P.; Maroulis, A. J. Synthesis of quinoxalines by cyclization of α-arylimino oximes of a-dicarbonyl compounds. Tetrahedron Lett. 2000, 41, 10299-10302;
26. (c) Antoniotti, S.; Duñach, E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines. Tetrahedron-Lett. 2002, 43, 3971-3973;
27. (d) Robinson, R. S.; Taylor, R. J. K. Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation. Synlett 2005, 1003-1005;
28. (e) Gopaland, D. V.; Subrahmanyam, M. Single-stepsynthesis of 2-methylquinoxaline from 1,2-phenylenediamine and 1,2-propanediol over modified HY zeolites. Catal. Commun. 2001, 219-223;
29. (f) Staszewska, A.; Stefanowicz, P.; Szewczuk, Z. Direct solid-phase synthesis of quinoxaline-containing peptides. Tetrahedron Lett. 2005, 46, 5525-5528;
30. 2 as a heterogeneous recyclable catalyst. TetrahedronLett. 2007, 48, 5371-5374.
31. (a) More, S. V.; Sastry, M. N. V.; Yao, C.-F. Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient and green approach for the synthesis of quinoxalines. Green Chem. 2006, 8, 91-95;
32. (b) Bhosale, R. S.; Sarda, S. R.; Ardhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst. Tetra hedron Lett. 2005, 46, 7183-7186;
33. (c) Darabi, H. R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature. Catal Commun. 2007, 389-392;
34. (d) Wang, L.; Liu, J.; Tian, H.; Qian, C. Ytterbium triflate catalyzed heterocyclization of 1,2-phenylenediamines and alkyl oxalates under solvent-free conditions via Phillips reaction: A facile synthesis of quinoxaline-2,3-diones derivatives. Synth. Commun. 2004, 34, 1349-1357;
35. (e) Hasaninejad, A.; Zare, A.; Mohammadizadeh, M. R.; Shekouhy, M. Oxalic acid as an efficient, cheap, and reusable catalyst for the preparation of quinoxalines via condensation of 1,2-diamines with α-diketones at room temperature. Arkivoc 2008, 8, 28-35;
36. (f) Heravi, M. M.; Bakhtiari, K.; Tehrani, M. H.; Javadi, N. M.; Oskooie, H. A. Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature. Arkivoc 2006, 16, 16-22;
37. (g) Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F.; Tehrani, M. H. Wells- Dawson type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature. Monatsh. Chem. 2007, 138, 465-467;
38. 4 at room temperature. Monatsh. Chem. 2007, 138, 875-877;
39. (i) Srinivas, C.; Kumar, C. N. S. S. P.; Rao, V. J.; Palaniappan, S. Efficient, convenient and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives. J. Mol. Cat. A: Chem. 2006, 265, 228-231.
40. Hasaninejad, A.; Parhami, A.; Zare, A.; Khalafi-Nezhad, A.; Nasrolahi Shirazi, A.; Moosavi Zare, A. R. Magnesium sulfate as an efficient and very cheap reagent for the preparation of bis(indolyl)methanes. Polish J. Chem.. 2008, 82, 565-569;
41. (b) Zare, A.; Hasaninejad, A.; Khalafi-Nezhad, A.; Parhami, A.; Moosavi Zare, A. R. A Solvent less protocol for the Michael addition of aromatic amidest to α,β-unsaturated esters promoted by microwave irradiation. J. Iran. Chem. Soc. 2008, 5, 100-105;
42. (c) Khalafi-Nezhad, A.; Parhami, A.; Zare, A.; Moosavi Zare, A. R.; Hasaninejad, A.; Panahi, F. Trityl chloride as a novel and efficient organic catalyst for room temperature preparation of bis(indolyl)methanes under solvent-free conditions in neutral Media. Synthesis 2008, 617-621;
43. 2: An efficient, green and heterogeneous catalytic system for the solvent-free synthesis of N-sulfonyl imines. Arkivoc 2008, 11, 64-74;
44. (e) Zare, A.; Hasaninejad, A.; Beyzavi, M. H.; Parhami, A.; Moosavi Zare, A. R.; Khalafi-Nezhad, A.; Sharghi, H. Zinc oxide-tetrabutylammonium bromide tandem as a highly efficient, green, and reusable catalyst for Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters under solvent-free conditions. Can. J. Chem. 2008, 86, 317-324.