Fluoroboric acid adsorbed on silica-gel-catalyzed synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives

Synthetic Communications

Volumn 39, Issue 4, 2009, Pages 580-589

  Liu, Yu Heng ^a   Tao, Xu Ye ^a   Lei, Li Qin ^a   Zhang, Zhan Hui ^a  

^a HEBEI NORMAL UNIVERSITY   (China)

Author keywords

naphthol; Aldehyde; HBF4 SiO2; Heterogeneous catalyst; Solvent free conditions; Xanthene

Indexed keywords

2 NAPHTHOL; ALDEHYDE; BORIC ACID; FLUOROBORIC ACID; SILICA GEL; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; COST; HEATING; POLYMERIZATION; SYNTHESIS;

EID: 61849132157     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802412842     Document Type: Article

References (42)

1. Griffiths, J.; Lee, W. J. Synthesis, light absorption and fluorescence properties of new thiazole analogues of the xanthene dyes. Dyes Pigments 2003, 57, 107-114.
2. Ahmad, M.; King, T. A.; Ko, D.-K.; Cha, B. H.; Lee, J. Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases. J. Phys. D: Appl. Phys. 2002, 35, 1473-1476.
3. Knight, C. G.; Stephens, T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles. Biochem. J. 1989, 258, 683-689.
4. Poupelin, J. P.; Saint-Rut, G.; Fussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lakroix, R. Synthesis and antiinflammatory properties of bis(2-hydroxy-1-naphthyl)methane derivatives, I: Monosubstituted derivatives. Eur. J. Med. Chem. 1978, 13, 67-71.
5. Ion, R. M.; Frackowiak, D.; Planner, A.; Wiktorowicz, K. The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption, and emission spectroscopy. Acta Biochim. Pol. 1998, 45, 833-845.
6. Amini, M. M.; Seyyedhamzeh, M.; Bazgir, A. Heteropolyacid: An efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]- xanthene. Appl. Catal. A: Gen. 2007, 323, 242-245.
7. Khosropour, A. R.; Khodaei, M. M.; Moghannian, H. A facile, simple, and convenient method for the synthesis of 14-alkyl and aryl-14H-dibenzo[a,j] xanthenes catalyzed by pTSA in solution and solvent-free conditions. Synlett 2005, 955-958.
8. Liu, D.; Yu, Y.; Shi, W.; Liu C.; Luo, G. A highly efficient solvent-free synthesis of benzoxanthenes catalyzed by methanesulfonic acid. Prep. Biochem. Biotechnol. 2007, 37, 77-81.
9. Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M. S.; Arzroomchilar, E. Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo [a,j]xanthenes in water. Bioorg. Med. Chem. 2008, 18, 436-438.
10. Selvam, N. P.; Shanthi, G.; Perumal, P. T. Ceric-sulfate-catalyzed synthesis of 14-aryl or alkyl-14H-dibenzo[aj]xanthenes under conventional heating and microwave irradiation. Can. J. Chem. 2007, 85, 989-995.
11. Saini, A.; Kumar, S.; Dandhu, J. S. A new LiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j] xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating. Synlett 2006, 1928-1932.
12. Pasha, M. A.; Jayashankara, V. P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free condition. Bioorg. Med. Chem. 2007, 17, 621-623.
13. Rajitha, B.; Kumar B. S.; Reddy, Y. T.; Reddy, P. N.; Sreenivasulu, N. Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a.j]xanthenes under conventional heating and microwave irradiation. Tetrahedron Lett. 2005, 46, 8691-8693.
14. 2 as heterogeneous catalysts under conventional heating in a solvent-free media. Synth. Commun. 2007, 37, 2519-2525.
15. Ko, S.; Yao, C.-F. Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions. Tetrahedron Lett. 2006, 47, 8827-8829.
16. 2): A mild, reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j] xanthenes. J. Mol. Catal. A: Chem. 2007, 275, 25-29.
17. Patil, S. B.; Bhat, R. P.; Samant, S. D. Cation-exchange resins: Efficient heterogeneous catalysts for facile synthesis of dibenzoxanthene from β-naphthol and aldehydes. Synth. Commun. 2006, 36, 2163-2168.
18. Shakibaei, G. I.; Mirzaei, P.; Bazgir, A. Dowex-50W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions. Appl. Catal. A: Gen. 2007, 325, 188-192.
19. 2O): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a.j]xanthenes under conventional heating and microwave irradiation. Catal. Commun. 2007, 8, 1173-1177.
20. Kumari, P.; Yathindranath, V.; Chauan, S. M. S. Facile and efficient synthesis of 14-alkyl-oraryl-14-H-dibenzo[a,j]xanthenes using sulfonylfunctionalized ionic liquids. Synth. Commun. 2008, 38, 637-648.
21. Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. Wet cyanuric chloride catalysed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]-xanthenes. Catal. Commun. 2007, 8, 1595-1598.
22. Solinas, A.; Taddei, M. Solid-supported reagents and catch-and-release techniques inorganic synthesis. Synthesis 2007, 2409-2453.
23. Chakraborti, A. K.; Gulhane, R. Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines. TetrahedronLett. 2003, 44, 3521-3525.
24. Bandgar, B. P.; Patil, A. V. Fluoroboric acid adsorbed on silica gel catalysed regioselective ring opening of epoxides with nitrogen heterocycles. Tetrahedron Lett. 2007, 48, 173-176.
25. Kumar, D.; Kumar, R.; Chakraborti, A. K. Tetrafluoroboric acid adsorbed on silica gel as a reusable heterogeneous dual-purpose catalyst for conversion of aldehydes/ketones into acetals/ketals and back again. Synthesis 2008, 1249-1256.
26. 2-catalyzed synthesis of acylals from aldehydes under solvent-free conditions. Synlett 2006, 2719-2722.
27. Bandgar, B. P.; Patil, A. V.; Chavan, O. S. Silica supported fluoroboric acid as a novel, efficient, and reusable catalyst for the synthesis of 1,5-benzodiazepines under solvent-free conditions. J. Mol. Catal. A: Chem. 2006, 256, 99-105.
28. Chen, W. Y.; Li, X. S: Lu, J. Mannich-type reaction catalyzed by silica-supported fluoroboric acid under solvent-free conditions. Synth. Commun. 2008, 38, 546-552.
29. 2) as a new, highly efficient, and reusable heterogeneous catalyst for thia-Michael addition to a,b-unsaturated carbonyl compounds. Tetrahedron Lett. 2008, 49, 4272-4275.
30. 2. J. Mol. Catal. A: Chem. 2007, 268, 70-75.
31. 2) as a catalyst under mild conditions in the absence of solvent. J. Mol. Catal. A: Chem. 2007, 273, 114-117.
32. (a) Zhang, Z.-H.; Tao, X.-Y. 2,4,6-Trichloro-1,3,5-triazine-promoted synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions. Aust. J. Chem. 2008, 61, 77-79;
33. (b) Zhang, Z.-H. Sodium hydrogen sulfate in poly (ethylene glycol). An efficient recyclable system for the deprotection of 1,1-diacetates. Monatsh. Chem. 2005, 136, 1191-1195;
34. 2-catalyzed synthesis of bis(indolyl)methanes. Synth. Commun. 2005, 35, 1997-2004;
35. (d) Zhang, Z.-H.; Hu, J.-Y. Cobalt(II) chloride-mediated synthesis of β-enamino compounds under solvent-free conditions. J. Braz. Chem. Soc. 2006, 17, 1447-1451;
36. (e) Zhang, Z.-H.; Yang, S.-T.; Lin, J. Mild and effcient procedure for the synthesis of 1,5-benzodiazepines catalyzed by magnesium perchlorate. Synth. Commun. 2006, 36, 1645-1654;
37. (f) Zhang, Z.-H.; Lin, J. Effcient and convenient method for the synthesis of symmetrical triindolylmethanes catalyzed by iodine. Synth. Commun. 2007, 37, 209-215;
38. 2O. Catal. Commun. 2007, 8, 1615-1620;
39. (h) Zhang, Z.-H.; Li, J.-J.; Gao, Y.-Z.; Liu, Y.-H. Synthesis of 2-substituted benzimidazoles by iodine-mediated condensation of orthoesters with 1,2-phenylenediamines. J. Heterocycl. Chem. 2007, 44, 1509-1512;
40. (i) Zhang, Z.-H.; Li, T.-S.; Li, J.-J. A highly effective sulfamic acid/methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature. Monatsh. Chem. 2007, 138, 89-94;
41. 2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones. Catal. Commun. 2008, 9, 1715-1719;
42. (k) Zhang, Z.-H.; Li, J.-J.; Li, T.-S. Ultrasound-assisted synthesis of pyrroles catalyzed by zirconium chloride under solvent-free conditions. Ultrason. Sonochem. 2008, 15, 673-676.