N-sulfonic acid poly(4-vinylpyridinium) chloride: A novel polymeric and reusable catalyst for the preparation of xanthenes derivatives

Dyes and Pigments

Volumn 99, Issue 1, 2013, Pages 250-255

  Shirini, Frahad ^a   Abedini, Masoumeh ^a   Pourhasan, Reyhaneh ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

1,8 Dioxo octahydroxanthene; 14 Aryl 14H dibenzo a,j xanthenes; N sulfonic acid poly(4 vinylpyridinium) chloride (NSPVPC); Reusable catalyst; Solvent free conditions; Tetrahydrobenzo a xanthene 11 ones

Indexed keywords

1 ,8-DIOXO-OCTAHYDROXANTHENE; N-SULFONIC ACID POLY(4-VINYLPYRIDINIUM) CHLORIDE (NSPVPC); REUSABLE CATALYSTS; SOLVENT FREE CONDITIONS; TETRAHYDROBENZO[A]XANTHENE-11- ONES;

CHLORINE COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; XANTHENES;

CATALYSTS;

EID: 84884901685     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.04.036     Document Type: Article

References (50)

1. Lamberk RW, Martin JA, Merrett JH, Parkes KEB, Thomas G. J. PCT Int. Appl. WO 9706178 (1997). Chem Abstr 1997;126:P212377y.
2. Hideu T. JPn. Tokkyo Koho JP 56005480 (1981). Chem Abstr 1981;95:80922b.
3. J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narciss, G. Uchida Ernouf, and R. Lakroix Synthesis and antiinflammatory properties of bis (2 hydroxy 1 naphthyl) methane derivatives Eur J Med Chem 13 1978 67 71 (Pubitemid 8293247)
4. G. Saint-Ruf, A. De, and H.T. Hieu The effect of dibenzoxanthenes on the paralyzing action of zoxazolamine Naturwissenschaften 62 1975 584 585
5. R.M. Ion, D. Frackowiak, A. Planner, and K. Wiktorowicz The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy Acta Biochim Pol 45 1998 833 845 (Pubitemid 128434271)
6. Y. Kitahara, and K. Tanaka Synthesis, crystal structure and properties of thiaheterohelicenes containing phenolic hydroxy functions Chem Commun 2002 932 933 (Pubitemid 34494085)
7. M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, and J. Lee Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases J Phys D Appl Phys 35 2002 1473 1476 (Pubitemid 34789713)
8. C.G. Knight, and T. Stephens Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles J Biochem 258 1989 683 687
9. Z.Y. Lu, Z.J. Lin, W.L. Wang, L. Du, T.J. Zhu, and Y.C. Fang Citrinin dimers from the halotolerant fungus Penicillium citrinum B-57 J Nat Prod 71 2008 543 546 (Pubitemid 351656183)
10. A.R. Carroll, J. Lamb, R. Moni, G.P. Guymer, P.I. Forster, and R.J. Quinn Myrtucommulones F-I, phloroglucinols with thyrotropin-releasing hormone receptor-2 binding affinity from the seeds of corymbia scabrida J Nat Prod 71 2008 1564 1568
11. F. Shaheen, M. Ahmad, S.N. Khan, S.S. Hussain, S. Anjum, and B. Tashkhodjaev New α-glucosidase inhibitors and antibacterial compounds from Myrtus communis L. Eur J Org Chem 2006 2371 2377
12. P.S. Kumar, B.S. Kumar, B. Rajitha, P.N. Reddy, N. Sreenivasulu, and Y.T. Reddy A novel one pot synthesis of 14-aryl-14H-dibenzo[a, j]xanthenes catalyzed by Selectfluor™ under solvent free conditions ARKIVOC xii 2006 46 50 (Pubitemid 44124849)
13. M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, and E. Arzroomchilar Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a, j]xanthenes in water Bioorg Med Chem Lett 18 2008 436 438
14. 2: an eco-friendly and re-usable catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a, j]xanthenes J Iran Chem Soc 8 2011 129 134
15. 2 with high recyclability RSC Adv 3 2013 1323 1326
16. A. Rahmatpour An efficient, high yielding, and eco-friendly method for the synthesis of 14-aryl- or 14-alkyl-14H-dibenzo[a, j]xanthenes using polyvinylsulfonic acid as a recyclable Bronsted acid catalyst Monatsh Chem 142 2011 1259 1263
17. 2 - a versatile and efficient catalyst for synthesis of 14-aryl-or 14-alkyl-15H-dibenzo [a, j] xanthenes Chem Heterocycl Compd 48 2012 856 860
18. J. Safaei-Ghomi, and M.A. Ghasemzadeh Zinc oxide nanoparticles: a highly efficient and readily recycylable catalyst for the synthesis of xanthenes Chin Chem Lett 23 2012 1225 1229
19. B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, and B.V. Rao Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a, j]xanthenes J Mol Catal A Chem 255 2006 74 77 (Pubitemid 44067554)
20. M.A. Pasha, and V.P. Jayashankara Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a, j]xanthenes under solvent-free condition Bioorg Med Chem Lett 17 2007 621 623 (Pubitemid 46108575)
21. H.R. Shaterian, M. Ghashang, and A. Hassankhani One-pot synthesis of aryl-14H- dibenzo[a, j]xanthene leuco-dye derivatives Dye Pigment 76 2008 564 568 (Pubitemid 47382571)
22. M. Seyyedhamzeh, P. Mirzaei, and A. Bazgir Solvent-free synthesis of aryl-14H-dibenzo[a, j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst Dye Pigment 76 2008 836 839 (Pubitemid 47412973)
23. 3H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of β-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a, j]xanthenes J Mol Liq 167 2012 69 77
24. A. Zare, M. Mokhlesi, A.R. Hasaninejad, and T. Hekmat-Zadeh Solvent-free synthesis of 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a, j]xanthenes using saccharin sulfonic acid as an efficient and green catalyst E J Chem 9 2012 1854 1863
25. 2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones Catal Commun 9 2008 1715 1719
26. 3H) as an efficient and reusable heterogeneous catalyst for the one-pot synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions Chin Chem Lett 20 2009 539 541
27. 3H as a nanoreactor, nanocatalyst in aqueous media Ultrason Sonochem 17 2010 306 309
28. T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang, and T.S. Li Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by p- dodecylbenezenesulfonic acid in aqueous media Synlett 5 2004 866 870
29. X.S. Wang, D.Q. Shi, Y.L. Li, H. Chen, X.Y. Wei, and Z.M. Zong A clean synthesis of 1-oxo-hexahydroxanthene derivatives in aqueous media catalyzed by TEBA Synth Commun 35 2005 97 104 (Pubitemid 40270839)
30. F. Darvish, S. Balalaei, F. Chadegani, and P. Salehi Diammonium hydrogen phosphate as a neutral and efficient catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives in aqueous media Synth Commun 37 2007 1059 1066 (Pubitemid 46568926)
31. A. Javid, M.M. Heravi, and F.F. Bamoharram One-pot synthesis of 1,8-dioxo-octahydroxanthenes utilizing silica-supported preyssler nano particles as novel and efficient reusable heterogeneous acidic catalyst E J Chem 8 2011 910 916
32. M.M. Heravi, H. Alinejhad, K. Bakhtiari, and H.A. Oskooie Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7, 8,10-tetrahydro-9H-[1,3]-dioxolo [4,5-b]xanthen-9-ones and 12-aryl-9,9-dimethyl- 8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones Mol Divers 14 2010 621 626
33. F. Shirini, and N. Ghaffari Khaligh Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthenes derivatives under solvent-free conditions Dye Pigment 95 2012 789 794
34. H.J. Wang, X.Q. Ren, Y.Y. Zhang, and Z.H. Zhang Synthesis 12-aryl or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by dodecatungstophosphoric acid J Braz Chem Soc 20 2009 1939 1943
35. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, and Z. Asgari Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media Catal Commun 20 2012 54 57
36. G.C. Nandi, S. Samai, R. Kumar, and M.S. Singh An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11- dione derivatives under solvent free condition Tetrahedron 65 2009 7129 7134
37. B. Maleki, S. Barzegar, Z. Sepehr, M. Kermanian, and R. Tayebee A novel polymeric catalyst for the one-pot synthesis of xanthenes derivatives under solvent-free conditions J Iran Chem Soc 9 2012 757 765
38. F. Shirini, and O. Goli Jolodar Introduction of N-sulfonic acid poly(4-vinylpyridinum) chloride as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes J Mol Catal A Chem 356 2012 61 69
39. F. Shirini, M.A. Zolfigol, and M. Abedini Chemoselective trimethylsilylation of alcohols catalyzed by saccharin sulfonic acid Monatsh Chem 140 2009 61 64
40. F. Shirini, M.A. Zolfigol, and M. Abedini Saccharinsulfonic acid: an efficient and recyclable catalyst for acetylation of alcohols, phenols and amines Monatsh Chem 140 2009 1495 1498
41. F. Shirini, M.A. Zolfigol, and M. Abedini Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tert-butyl ethers from alcohols J Iran Chem Soc 7 2010 603 607
42. F. Shirini, M.A. Zolfigol, and J. Albadi Melamine trisulfonic acid (MTSA): a new efficient catalyst for the chemoselective methoxymethylation of alcohols Synth Commun 40 2010 910 914
43. F. Shirini, M.A. Zolfigol, A.R. Aliakbar, and J. Albadi Efficient acetylation of alcohols, phenols, and amines catalyzed by melamine trisulfonic acid (MTSA) Synth Commun 40 2010 1022 1028
44. F. Shirini, M.A. Zolfigol, and J. Albadi Melamine trisulfonic acid: a new, efficient and recyclable catalyst for the synthesis of 3,4- dihydropyrimidin-2(1H)-ones/thiones in the absence of solvent Chin Chem Lett 22 2011 318 321
45. F. Shirini, M.A. Zolfigol, and J. Albadi Melamine trisulfonic acid as a new, efficient and reusable catalyst for the solvent free synthesis of coumarins J Iran Chem Soc 7 2010 895 899
46. F. Shirini, and N.G. Khaligh Succinimide-N-sulfonic acid: a mild, efficient, and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols Phosphorus Sulfur Silicon 186 2011 2156 2165
47. F. Shirini, and N.G. Khaligh Succinimide sulfonic acid (SuSA): an efficient and recyclable catalyst for the chemoselective N-Boc protection of amines Monatsh Chem 143 2012 631 635
48. F. Shirini, N.G. Khaligh, and O. Goli Jolodar N-Sulfonic acid poly(4-vinylpyridinium) chloride: an efficient and reusable solid acid catalyst in N-Boc protection of amines J Iran Chem Soc 10 2013 181 188
49. M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, and Z. Asgari Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts C R Chim 15 2012 719 736
50. L. Li-Bin, J. Tong-Shou, H. Li-Sha, L. Meng, Q. Na, and L. Tong-Shuang The reaction of aromatic aldehydes and 1,3-cyclohexanedione in aqueous media E J Chem 3 2006 117 121