One-pot synthesis of xanthene derivatives under solvent-free conditions

Chemical Papers

Volumn 62, Issue 5, 2008, Pages 522-526

  Dabiri, Minoo ^a   Azimi, Seyyedeh C ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Montmorillonite K10; Naphthol; Reusable catalyst; Solvent free; Xanthenes

Indexed keywords

EID: 49649092636     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-008-0050-y     Document Type: Article

References (33)

1. M. Ahmad T. A. King D.-K. Ko B. H. Cha J. Lee 2002 Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases Journal of Physics D: Applied Physics 35 1473 1476
2. M. M. Amini M. Seyyedhamzeh A. Bazgir 2007 Heteropolyacid: An efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene Applied Catalalysis A: General 323 242 245
3. 2): A mild, reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes Journal of Molecular Catalalysis A: Chemical 275 25 29
4. B. Das B. Ravikanth R. Ramu K. Laxminarayana B. V. Rao 2006 Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j] xanthenes Journal of Molecular Catalysis A: Chemical 255 74 77
5. B. Das P. Thirupathi I. Mahender V. Saidi Reddy Y. Koteswara Rao 2006 Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines Journal of Molecular Catalalysis A: Chemical 247 233 239
6. B. Das P. Thirupathi K. Ravinder Reddy B. Ravikanth L. Nagarapu 2007 An efficient synthesis of 1,8-dioxo-octahydroxanthenes using heterogeneous catalysts Catalysis Communications 8 535 538
7. 2O-promoted green preparation of xanthenedione derivatives in ionic liquids Canadian Journal of Chemistry 83 16 20
8. A. Jha J. Beal 2004 Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone Tetrahedron Letters 45 8999 9001
9. T.-S. Jin J.-S. Zhang A.-Q. Wang T.-S. Li 2005 Solid-state condensation reactions between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature Synthetic Communications 35 2339 2345
10. A. Khoramabadi-zad Z. Kazemi H. Amiri Rudbari 2002 Structural investigation and preparation of 14-alkyl-14H-dibenzo[a,j]xanthenes revised Journal of the Korean Chemical Society 46 541 544
11. A. R. Khosropour M. M. Khodaei H. Moghannian 2005 A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j] xanthenes catalyzed by pTSA in solution and solvent-free conditions Synlett 2005 955 958
12. Y. Kitahara K. Tanaka 2002 Synthesis, crystal structure and properties of thiaheterohelicenes containing phenolic hydroxy functions Chemical Communications 2002 932 933
13. D. W. Knight P. B. Little 2001 The first efficient method for the intramolecular trapping of benzynes by phenols: A new approach to xanthenes Journal of the Chemical Society, Perkin Transactions 1 14 1771 1777
14. C. G. Knight T. Stephens 1989 Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles Biochemical Journal 258 683 687
15. S. Ko C.-F. Yao 2006 Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions Tetrahedron Letters 47 8827 8829
16. Kozhevnikov, I. V. (2002). Catalysts for fine chemical synthesis, Vol. 2, Catalysis by polyoxometalates. New York: Wiley.
17. P. S. Kumar B. Sunil Kumar B. Rajitha P. Narsimha Reddy N. Sreenivasulu Y. Thirupathi Reddy 2006 A novel one pot synthesis of 14-aryl-14H-dibenzo[a,j] xanthenes catalyzed by Selectfluor™ under solvent free conditions Arkivoc xii 46 50
18. Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B., & Thomas, G. J. (1997). PCT Int. Appl. WO9706178.
19. L. Nagarapu S. Kantevari V. C. Mahankhali S. Apuri 2007 Potassium dodecatungstocobaltate trihydrate (Kco WO • 3HO): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation Catalysis Communications 8 1173 1177
20. K. Ota T. Kito 1976 An improved synthesis of dibenzoxanthene Bulletin of the Chemical Society of Japan 49 1167 1168
21. P. Papini R. Cimmarusti 1947 The action of formamide and formanilide on naphthols and on barbituric acid Gazzetta Chimica Italiana 77 142 147
22. M. A. Pasha V. P. Jayashankara 2007 Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free condition Bioorganic & Medicinal Chemistry Letters 17 621 623
23. S. B. Patil R. P. Bhat S. D. Samant 2006 Cation-exchange resins: Efficient heterogeneous catalysts for facile synthesis of dibenzoxanthene from β-naphthol and aldehydes Synthetic Communications 36 2163 2168
24. J. P. Poupelin G. Saint-Ruf O. Foussard-Blanpin G. Narcisse G. Uchida-Ernouf R. Lacroix 1978 Synthesis and antiinflammatory properties of bis (2-hydroxy-1-naphthyl)methane derivatives I European Journal of Medicinal Chemistry 13 67 71
25. B. Rajitha B. Sunil Kumar Y. Thirupathi Reddy P. Narsimha Reddy N. Sreenivasulu 2005 Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation Tetrahedron Letters 46 8691 8693
26. P. Rashidi-Ranjbar A. Mohajeri A. H. Mohmoudkhani 2001 Revision of the structure and stereochemistry of the 2-naphthol-acetaldehyde 2:2 condensation product. A study by X-ray crystallography and the AM1 method Journal of Physical Organic Chemistry 14 210 216
27. A. Saini S. Kumar J. S. Sandhu 2006 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
28. R. J. Sarma J. B. Baruah 2005 One step synthesis of dibenzoxanthenes Dyes and Pigments 64 91 92
29. R. N. Sen N. N. Sarkar 1925 The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds Journal of the American Chemical Society 47 1079 1091
30. M. Seyyedhamzeh P. Mirzaei A. Bazgir 2007 Solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst Dyes and Pigments 76 836 839
31. G. I. Shakibaei P. Mirzaei A. Bazgir 2007 Dowex-50W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions Applied Catalalysis A: General 325 188 192
32. Takeshiba, H., & Jiyoujima, T. (1981). Japan Kokai Tokkyo Koho JP 56005480. Tokyo: Japan Patent Office.
33. 2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions Tetrahedron 57 9509 9511