Citation: Farhad Shirini, Asieh Yahyazadeh, Kamal Mohammadi. One-pot synthesis of various xanthene derivatives using ionic liquid 1, 3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst under solvent-free conditions[J]. Chinese Chemical Letters, ;2014, 25(2): 341-347. shu

One-pot synthesis of various xanthene derivatives using ionic liquid 1, 3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst under solvent-free conditions

1.
Department of Chemistry, College of Science, University of Guilan, Rasht 41335, Iran

Corresponding author: Farhad Shirini, Asieh Yahyazadeh,
Received Date: 8 August 2013
Available Online: 23 October 2013

In this study, 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHS) is used as an efficient and reusable ionic liquid for the green, mild, and efficient synthesis of xanthenes under solvent-free conditions. Simple and easy work-up, low cost, green process, short reaction times and excellent yields of the products are the advantages of this procedure. Further, the catalyst can be recycled and reused at least for four times without a noticeably decrease in its catalytic activity.
- Xanthene derivatives,
- One-pot reaction,
- 1,3-Disulfonic acid imidazolium hydrogen,
- sulfate Ionic,
- liquid Solvent-free conditions
1. [1]
  [1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, UK, 1998.
2. [2]
  [2] M. Poliakoff, M.J. Fitzpatric, T.R. Farren, P.T. Anastas, Green chemistry: science and politics of change, Science 297 (2002) 807-810.
3. [3]
  [3] I.T. Horváth, P.T. Anastas, Innovations and green chemistry, Chem. Rev. 107 (2007) 2169-2173.
4. [4]
  [4] T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev. 99 (1999) 2071-2084.
5. [5]
  [5] T. Welton, Ionic liquids in catalysis, Coord. Chem. Rev. 248 (2004) 2459- 2477.
6. [6]
  [6] P. Wasserscheid, W. Keim, Ionic liquids-new "solutions" for transition metal catalysis, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.
7. [7]
  [7] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, 3-Methyl-1-sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature, J. Iran. Chem. Soc. 7 (2010) 646-651.
8. [8]
  [8] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Ionic liquid 3-methyl-1- sulfonic acid imidazolium chloride as a novel and highly efficient catalyst for the very rapid synthesis of bis(indolyl)methanes under solvent-free conditions, Org. Prep. Proced. Int. 42 (2010) 95-102.
9. [9]
  [9] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, An efficient method for the nitration of phenols with nano2 in the presence of 3-methyl-1-sulfonic acid imidazolium, Sci. Iran. Trans. C: Chem. Chem. Eng. 17 (2010) 31-36.
10. [10]
  [10] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts, Appl. Catal. A: Gen. 400 (2011) 70-81.
11. [11]
  [11] S.L. Schreiber, Target-oriented and diversity-oriented organic synthesis in drug discovery, Science 287 (2000) 1964-1969.
12. [12]
  [12] A. Domling, Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol. 6 (2002) 306-313.
13. [13]
  [13] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2005.
14. [14]
  [14] V. Polshettiwar, R.S. Varma, Greener and expeditious synthesis of bioactive heterocycles using microwave irradiation, Pure. Appl. Chem. 80 (2008) 777-790.
15. [15]
  [15] A. Hasaninejad, A. Zare, M. Shekouhy, Highly efficient synthesis of triazolo[1, 2- a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent- free conditions, Tetrahedron 67 (2011) 390-400.
16. [16]
  [16] S. Stavber, Recent advances in the application of selectfluor^TM F-TEDA-BF4 as a versatile mediator or catalyst in organic synthesis, Molecules 16 (2011) 6432- 6464.
17. [17]
  [17] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, et al., H₄SiW₁₂O₄₀ catalyzed onepot synthesis of 12-aryl-8, 9,10,12-tetrahydrobenzo[a] xanthen-11-ones under solvent-free conditions, Eur. J. Med. Chem. 13 (1978) 67-71.
18. [18]
  [18] J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes, Cell. Biol. Int. Rep. 14 (1990) 1075-1084.
19. [19]
  [19] G.W. Rewcastle, G.J. Atwell, L. Zhuang, B.C. Baguley, W.A. Denny, Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids, J. Med. Chem. 34 (1991) 217-222.
20. [20]
  [20] A.T. Peters, M.J. Bide, Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres, Dyes Pigm. 6 (1985) 349-375.
21. [21]
  [21] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-687.
22. [22]
  [22] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
23. [23]
  [23] A. Bekaert, J. Andrieux, M. Plat, New total synthesis of bikaverin, Tetrahedron Lett. 33 (1992) 2805-2806.
24. [24]
  [24] D.W. Knight, P.B. Little, The first efficient method for the intramolecular trapping of benzynes by phenols: a new approach to xanthenes, J. Chem. Soc. Perkin Trans. 1 15 (2001) 1771-1777.
25. [25]
  [25] C.W. Kuo, J.M. Fang, Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions, Synth. Commun. 31 (2001) 877-892.
26. [26]
  [26] J.Q. Wang, R.G. Harvey, Synthesis of polycyclic xanthenes and furans via palladium- catalyzed cyclization of polycyclic aryltriflate esters, Tetrahedron 58 (2002) 5927-5931.
27. [27]
  [27] H.R. Shaterian, A. Hosseinian, M. Ghashang, Ferric hydrogen sulfate as an efficient heterogeneous catalyst for environmentally friendly greener synthesis of 1,8- dioxo-octahydroxanthenes, Turk. J. Chem. 33 (2009) 233-240.
28. [28]
  [28] J. Li, L. Lu, W. Su, A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water, Tetrahedron Lett. 51 (2010) 2434-2437.
29. [29]
  [29] B. Das, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives, Synlett (2007) 3107-3112.
30. [30]
  [30] J. Li, W. Tang, L. Lu, W. Su, Strontium triflate catalyzed one-pot condensation of bnaphthol, aldehydes and cyclic 1,3-dicarbonyl compounds, Tetrahedron Lett. 49 (2008) 7117-7120.
31. [31]
  [31] N. Foroughifar, A. Mobinikhaledi, H. Moghanian, A catalytic and green procedure for synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11- one derivatives under solvent-free conditions, Int. J. Green Nanotechnol. Phys. Chem. 1 (2009) 57-63.
32. [32]
  [32] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M.K. Jalali, One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst, Can. J. Chem. 89 (2011) 623-627.
33. [33]
  [33] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j] xanthenes catalyzed by P₂O₅/Al₂O₃ under microwave irradiation, Dyes Pigm. 85 (2010) 133-138.
34. [34]
  [34] B.B. Mirjalili, A. Bamoniri, A. Akbari, BF₃·SiO₂: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 6454-6456.
35. [35]
  [35] N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Oxalic acid as a catalyst for efficient synthesis of bis-(indolyl)methanes, and 14-aryl-14H-dibenzo[a,j]xanthenes in water, Chin. Chem. Lett. 19 (2008) 1186-1189.
36. [36]
  [36] F. Shirini, N.G. Khaligh, G.H. Imanzadeh, P.G. Ghasem-Abadi, 1,3-Dibromo-5,5- dimethylhydantoin (DBH)/kaolin: an efficient reagent system for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 1145-1148.
37. [37]
  [37] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.
38. [38]
  [38] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B.V. Rao, Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, J. Mol. Catal. A: Chem. 255 (2006) 74-77.
39. [39]
  [39] A.P. Mohamed, P.J. Vaderapura, Molecular iodine catalyzed synthesis of aryl-14Hdibenzo[a,j]xanthenes under solvent-free condition, Bioorg. Med. Chem. Lett. 17 (2007) 621-623.
40. [40]
  [40] M. Mohammadpour Amini, M. Seyyedhamzeh, A. Bazgir, Heteropolyacid: an efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]- xanthene, Appl. Catal. A: Gen. 323 (2007) 242-245.
41. [41]
  [41] M.M. Heravi, Kh. Bakhtiari, Z. Daro@gheha, F.F. Bamoharram, Facile heteropolyacid- promoted synthesis of 14-substituted-14-H-dibenzo[a,j] xanthene derivatives under solvent-free conditions, J. Mol. Catal. A: Chem. 273 (2007) 99-101.
42. [42]
  [42] H.R. Shaterian, M. Ghashang, A. Hassankhani, One-pot synthesis of aryl 14Hdibenzo[a,j]xanthene leuco-dye derivatives, Dyes Pigm. 76 (2008) 564-568.
43. [43]
  [43] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Solvent-free synthesis of aryl-14Hdibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst, Dyes Pigm. 76 (2008) 836-839.
44. [44]
  [44] S. Ko, C.F. Yao, Heterogeneous catalyst: amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Tetrahedron Lett. 47 (2006) 8827-8829.
45. [45]
  [45] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, Nano-TiO2: 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) S129-S134.
46. [46]
  [46] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, 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.
47. [47]
  [47] H.J. Zang, Y. Zhang, B.W. Cheng, Efficient one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-one derivatives using NaHSO4 as catalyst in ionic liquid, Adv. Mater. Res. 113 (2010) 1993-1996.
48. [48]
  [48] A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei, A. Zolfaghari, Facile montmorillonite k-10-supported synthesis of xanthene derivatives under microwave and thermal conditions, Synth. Commun. 38 (2008) 2958-2966.
49. [49]
  [49] A.R. Khosropour,M.M. Khodaei, H.Moghannian, A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions, Synlett (2005) 955- 958.
50. [50]
  [50] N.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, Catal Commun. 8 (2007) 1595-1598.
51. [51]
  [51] S. Allameh, A. Davoodnia, A. Khojastehnezhad, An efficient and eco-friendly synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes using H₄[SiW₁₂O₄₀] as a heterogeneous and reusable catalyst under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 17-20.
52. [52]
  [52] W. Su, D. Yang, C. Jin, B. Zhang, Yb(OTf)₃ catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 3391-3394.
53. [53]
  [53] F. Shirini, N.G. Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigm. 95 (2012) 789-794.
54. [54]
  [54] F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogenfree and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes, J. Mol. Catal. A: Chem. 365 (2012) 15-23.
55. [55]
  [55] F. Shirini, N.G. Khaligh, 1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines, J. Mol. Liq. 177 (2013) 386-393.
56. [56]
  [56] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, A study for the synthesis of dibenzo [a,j] xanthenes and 1-amidoalkyl 2-naphthols catalyzed by [Hmim][HSO4] as a green, efficient and reusable catalyst under solvent-free conditions, Iran. J. Catal. 1 (2011) 1-10.
57. [57]
  [57] G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani, Z. Emdadi, Ultrasound-promoted greener synthesis of aryl-14-H-dibenzo[a,j]xanthenes catalyzed by NH₄H₂PO₄/ SiO₂ in water, Ultrason. Sonochem. 16 (2009) 7-10.
58. [58]
  [58] B. Maleki, M. Gholizadeh, Z. Sepehr, 1,3,5-Trichloro-2,4,6-triazinetrion: a versatile heterocycle for the one-pot synthesis of 14-aryl- or alkyl-14H-dibenzo[a,j]- xanthene, 1,8-dioxooctahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives under solvent-free conditions, Bull. Korean Chem. Soc. 32 (2011) 1697-1702.
59. [59]
  [59] H. Hashemi, A.R. Sardarian, 4-Dodecylbenzenesulfonic acid (DBSA) as an efficient and recyclable catalyst for synthesis of 14-aryl- and 14-alkyl-14-Hdibenzo[a,j]xanthenes under solvent-free conditions, Iran. J. Sci. Technol. A1 (2013) 75-82.
60. [60]
  [60] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, et al., 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.
61. [61]
  [61] G.C. Nandi, S. Samai, R. Kumar, 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.
62. [62]
  [62] M.M. Heravi, H. Alinejhad, K. Bakhtiari, 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.
63. [63]
  [63] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, A.R. Aliakbar, Rice husk: a mild, efficient, green and recyclable catalyst for the synthesis of 12-aryl- 8,9,10,12-tetrahydro[a]xanthene-11-ones and quinoxaline derivatives, C.R. Chim. 16 (2013) 207-216.
64. [64]
  [64] K. Venkatesan, S.S. Pujari, R.J. Lahoti, K.V. Srinivasan, An efficient synthesis of 1,8- dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation, Ultrason. Sonochem. 15 (2008) 548-553.
65. [65]
  [65] S. Kokkirala, N.M. Sabbavarapu, V.D.N. Yadavalli, b-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water, Eur. J. Chem. 2 (2011) 272-275.
66. [66]
  [66] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, et al., Ionic liquid triethylaminebonded sulfonic acid {[Et₃N-SO₃H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of b-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes, J. Mol. Liq. 167 (2012) 69-77.
67. [67]
  [67] S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, G. Amiri, H. Sepehrian, Ultrasound promoted rapid and green synthesis of 1,8-dioxo-octahydroxanthenes derivatives using nanosized MCM-41-SO3H as a nanoreactor, nanocatalyst in aqueous media, Ultrason. Sonochem. 17 (2010) 306-309.
68. [68]
  [68] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, et al., 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.
69. [69]
  [69] K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, The one-pot synthesis of 14-alkylor aryl-14H-dibenzo[a,j]xanthenes catalyzed by task-specific ionic liquid, Dyes Pigm. 80 (2009) 30-33.
70. [70]
  [70] D. Kundu, A. Majee, A. Hajra, Task-specific ionic liquid catalyzed efficient microwave- assisted synthesis of 12-alkyl or aryl-8,9,10,12-tetrahydrobenzo[a]xanthen- 11-ones under solvent-free conditions, Green Chem. Lett. Rev. 4 (2011) 205-209.
71. [71]
  [71] B. Janardhan, S. Vijaya Laxmi, B. Rajitha, An efficient synthesis of 12-aryl- 8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones using (4-sulfobutyl)tris(4-sulfophenyl) phosphonium hydrogen sulphate as catalyst under neat conditions, J. Chem. Pharm. Res. 4 (2012) 519-525.
72. [72]
  [72] J.M. Khurana, D. Magoo, pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions, Tetrahedron Lett. 50 (2009) 4777-4780.
73. [73]
  [73] A. Zare, R. Khanivar, M. Hatami, et al., Efficient synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-ones using ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO₄)₂} as a novel, green and homogeneous catalyst, J. Mex. Chem. Soc. 56 (2012) 389-394.
74. [74]
  [74] A. Zare, R. Khanivar, M. Merajoddin, et al., Triethylamine-bonded sulfonic acid {[Et₃N-SO₃H]Cl} as an efficient and homogeneous catalyst for the synthesis of 12- aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones, Iran. J. Catal. 2 (2012) 107- 114.
75. [75]
  [75] K. Niknam, M. Damya, 1-Butyl-3-methylimidazolium hydrogen sulfate[bmim]HSO4: an efficient reusable acidic ionic liquid for the synthesis of 1,8- dioxo-octahydroxanthenes, J. Chin. Chem. Soc. 56 (2009) 659-665.
76. [76]
  [76] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, 1-Methylimidazolium triflouroacetate ([Hmim]TFA): an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines, Catal. Commun. 9 (2008) 939.
77. [77]
  [77] M. Kalantari, Synthesis of 1,8-dioxo-octahydroxanthenes and bis(indolyl)- methanes catalyzed by [Et₃NH][H₂PO₄] as a cheap and mild acidic ionic liquid, Arabian J. Chem. 5 (2012) 319-323.
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11. [11]
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18. [18]
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19. [19]
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沈阳化工大学材料科学与工程学院沈阳 110142