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Applied Petrochemical Research

, Volume 8, Issue 2, pp 97–105 | Cite as

Preparation of a new, green and recyclable catalyst, silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride, and a solvent- and metal-free protocol for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives

  • Sami Sajjadifar
  • Maryam Pornuroz
Open Access
Original Article
  • 404 Downloads

Abstract

A cost-effective and convenient procedure for the synthesis of silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a recoverable heterogeneous and Brønsted acid catalyst is described, and was used for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent- and metal-free conditions at 110 °C in short reaction time with a yield of up to 95%. The present method offers several advantages such as simplicity in operation, ease of preparation and recycling of Brønsted acidic ionic liquid (BAIL), solvent-free reaction conditions, and no hazardous organic solvents are used in the entire procedure including workup and purification.

Graphical abstract

Keywords

1-(2-Sulfooxy)ethyl)1H-pyridine-1-ium-chloride One-pot reaction 14-Aryl-14H-dibenzo[a,j]xanthene Solvent- and metal-free conditions Brønsted acidic ionic liquid 

Introduction

Recently ionic liquids (ILs) are considered as dual reagents (catalysts and solvents) and a greener alternative for a range of various organic reactions, but the application of them as catalyst in the absence of solvent is vital and important in organic and inorganic chemistry [1]. As well as, ILs are an appropriate alternative instead of volatile and toxic organic solvents in the future due to high polarity, solubility with certain organic solvents and/or water, low vapor pressure, and excellent solubility in organic and inorganic materials [2]. On the other hand, ILs have been frequently used as solar cell, catalysts, biocatalysts, in nanomaterial synthesis, liquid–liquid separations, polymerization reactions, extraction, dissolution processes, electrochemistry and electrodeposition, and as supercapacitors [3, 4, 5, 6, 7, 8, 9, 10].

Among organic compounds, the synthesis of xanthene and its derivatives has received specific attention among pharmacological activities and organic chemists due to having a wide range of biological and therapeutic properties such as antioxidant [11], cytotoxic [12], anti-proliferative [13], antifungal [14], anti-inflammatory, antiviral [15], and antibacterial properties [16]. Furthermore, xanthene and its derivatives would be used in laser technologies [17], as pH-sensitive fluorescent materials for visualization of biomolecules [18], sensitisers in dye-sensitized solar cells (DSSCs) [19], in photodynamic therapy [20], as hole-transporting materials in organic light-emitting devices (OLEDs) [21], and in the food industry as additives [22]. Xanthene and its derivatives are available in natural plants [23, 24]. For instance, examples of natural xanthenes are 3-isopropyl-9a-methyl-1,2,4a,9a-tetrahydroxanthene A, used as an antidote for all snake venoms, blumeaxanthene B and lumeaxanthene C, used to treat gynecological disorders (Scheme 1).
Scheme 1

Examples of natural xanthenes

Different procedures have been employed for the preparation of xanthenes and benzoxanthenes [25, 26, 27, 28, 29]. In addition, one of the best, easiest, and cost-effective procedures for the synthesis of xanthene derivatives is condensation between aldehydes with 2-naphthols under different conditions in the presence of various Lewis and Brønsted acid catalysts such as Fe2(SO4)3.7H2O [30], polyvinylpolypyrrolidone-bound boron trifluoride [31], pentafluorophenyl ammonium triflate [32], silica sulfuric acid [33], γ-Fe2O3–HAp–Fe2+ NPs [34], H5PW10V2O40 [35], cellulose sulfuric acid [36], Yb(OTf)3 [37], 2,6-Pyridinedicarboxylic acid [38], silica-supported [2-(sulfooxy)ethyl]sulfamic acid [39], Selectfluor™ [40], carbon-based solid acid [41], I2 [42], ZnO NPs [43], p-toluenesulfonic acid/ionic liquid [44], trityl chloride [45], and polytungstozincate acid [46]. Although several of these procedures suffer from disadvantages such as the use of excess reagents/catalysts, tedious workup procedures, toxicity of the reagent, unsatisfactory yields, low yields of products, use of organic solvents, prolonged reaction time, use of the often expensive catalysts and non-recyclability, the focus on introducing efficient, economical, and solvent-free procedures with high activity, simple reaction workup, and reusability of the catalyst to overcome these problems is still in demand for the synthesis of xanthene derivatives.

It is necessary to introduce milder, simple reaction workup, solvent- and metal-free, faster, reusability of the catalyst, and generally a greener approach accompanied with higher yields for the synthesis of xanthene derivatives. Therefore, and according to the above-mentioned notes, it seems that silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a catalyst can be an appropriate in the synthesis of these organic compounds.

In this research, we wish to report a rapid and cost-effective procedure for the synthesis of silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a new, highly efficient, and Brønsted acid catalyst for the preparation of 14-aryl-14H-dibenzo[a,j]xanthene 3ap derivatives under solvent-, metal-free and thermal conditions (Scheme 2).
Scheme 2

One-pot synthesis of xanthene derivatives in the presence of BAIL under solvent-free conditions

Experimental

General

All of the reagents used in the current study were purchased from Merck, Aldrich, and Fluka and used without further purification. All the products are known compounds and were characterized by comparing the IR (KBr), 1H NMR, and 13C NMR spectroscopic data and their melting point to the literature values. Nuclear magnetic resonance (1H NMR and 13C NMR) was recorded in CDCl3 solvent on a Bruker DRX-300 and -400 spectrometer using tetramethylsilane (TMS) as an internal reference. IR spectra were recorded on a Frontier FT-IR (PerkinElmer) spectrometer using a KBr disk. The purities of the substrates and reaction monitoring were accomplished by TLC on silica gel PolyGram SILG/UV 254 plates. Melting points (MP) were determined on a Thermo Scientific 9300 melting point apparatus.

Preparation of silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl

In this study, silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a BAIL catalyst was prepared according to the literature procedure (Fig. 1) [47]. Spectral data of 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride are as follows: viscous brown oil: IR (KBr): OH (3200–3600 cm−1), C=N (1658 cm−1), C=C (1426 cm−1), S=O (1232 cm−1), and S–O (614 cm−1). 1H NMR (400 MHz, DMSO-d6): δ 3.13–3.16 (t, J = 5.6 Hz, 2H), 3.93–3.970 (t, J = 8 Hz, 2H), 8.10–8.17 (t, J = 12 Hz, 2H), 8.61 (s, 1H), 8.92–8.99 (t, J = 6.4 Hz, 2H), 9.00–9.42 (d, 1H). 13C NMR (100 MHz, DMSO-d6): 60.7, 61.8, 128.2, 142.2, 146.0.
Fig. 1

Pictures of reaction between pyridine and 2-chloroethanol (a), 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride (b), and silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride (c)

General procedure for the preparation of 14-aryl-14H-dibenzo[a,j]xanthenes

A mixture of 2-naphthol (1 mmol), various aldehydes (1 mmol) and SiO2/[SEP]Cl (20 mol%) in a 10-mL round-bottomed flask connected to a reflux condenser was stirred in an oil bath at 110 °C. Completion of the reaction was indicated by TLC (monitored by TLC, ethylacetate:n-hexane 1:3). After completion, the solvent was removed under reduced pressure and the crude product was recrystallized with ethanol to afford the pure product in 81–95% yield. All the products were known compounds and characterized by comparing the melting point, 1H NMR and 13C NMR spectra with those reported in the literature.

14-(4-Bromophenyl)-14H-dibenzo[a,j]xanthenes (Table 4, entry 3e)

1HNMR (300 MHz, CDCl3): δ 5.34 (1H, s, CH), 6.16–6.48 (10H, m, Ar–H), 6.68–6.75 (4H, m, Ar–H), 7.19–7.22 (2H, m, J = 7.8, Ar–H). 13CNMR (75 MHz, CDCl3): δ 37.46, 116.65, 118.01, 120.21, 122.39, 124.37, 126.92, 128.91, 129.11, 129.88, 131.04, 131.24, 131.58, 143.98, 148.67.

4-(4-Methoxyphenyl)-14H-dibenzo[a,j]xanthenes (Table 4, entry 3 g)

1H NMR (300 MHz, CDCl3): 2.49 (3H, s, OMe), 5.36 (1H, s, CH), 5.59–5.61 (2H, d, J = 8.66 Hz, Ar–H), 6.32–6.45 (6H, m, Ar–H), 6.49–6.55 (2H, m, Ar–H), 6.69–6.76 (4H, m, Ar–H), 7.31–7.33 (2H, d, J = 8.48, Ar–H); 13C NMR (75 MHz, CDCl3): 37.17, 55.05, 113.89, 117.58, 118.06, 122.77, 124.28, 126.81, 128.80, 128.87, 129.23, 131.13, 131.47, 137.45, 148.69, 157.89.

14-(2-Chlorophenyl)-14H-dibenzo[a,j]xanthenes (Table 4, entry 3 l)

1HNMR (300 MHz, CDCl3): δ 5.69 (1H, s, CH), 5.81–5.82 (2H, d, Ar–H), 6.27–6.40 (5H, m, Ar–H), 6.50 (2H, d, Ar–H), 6.55–6.67 (4H, m, Ar–H), 7.63–7.66 (2H, J = 8.5, d, Ar–H). 13CNMR (75 MHz, CDCl3): δ 34.63, 118.02, 118.11, 123.46, 124.44, 126.93, 127.87–127.94, 128.66, 129.08, 129.60, 130.13, 130.89, 131.76, 131.81, 143.57, 148.95.

Results and discussion

For this work, BAIL C as a green and reusable catalyst was prepared by condensation reaction between pyridine and 2-chloroethanol that led to ionic liquid B, following which chlorosulfonic acid was added dropwise and slowly to ionic liquid B for 45–60 min at 0 °C, which afforded BAIL C (Scheme 3) [47].
Scheme 3

The synthesis of 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride [SEP]Cl

The structure of 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride [SEP]Cl was characterized on the basis of its IR (KBr), 1H and 13C NMR data, which were presented in the “Experimental” section. The characterization of BAIL C in comparison to compounds A and B was further conducted by FT-IR spectrum (Fig. 2). As it can be seen from Fig. 2, the broad peak is at around 3200–3600 cm−1 which is related to the OH group. On the other hand, the spectra show that the broad peak is at around 1658 cm−1 for C=N and 1426 cm−1 for C=C, which imply both are related to pyridine ring, and the strong peak at 1232 cm−1 is related to the stretching vibration of S=O bond.
Fig. 2

Comparison of IR spectrum of compounds A and B with BAIL C

1H and 13C NMR spectra of the BAIL C are presented in Figs. 3 and 4. The important peaks of 1H NMR spectrum of BAIL C were related to the acidic hydrogen (SO3H) which was observed in 8.61 ppm. The 13C NMR spectrum of the BAIL C exhibited five signals in agreement with the proposed structure.
Fig. 3

1H NMR spectrum of [SEP]Cl

Fig. 4

13C NMR spectrum of [SEP]Cl

The activity of the new BAIL C as a reusable and green catalyst was tested using a one-pot condensation reaction of various aromatic aldehydes (1 mmol) with 2-naphthol (2 mmol) under solvent-free conditions for the preparation of biologically active 14-aryl-14H-dibenzo[a,j]xanthene derivatives (Scheme 2).

For this purpose, to optimize the reaction conditions for the synthesis of compound 3a, the condensation reaction of benzaldehyde (1 mmol) and 2-naphthol (2 mmol) was chosen using different amounts of BAIL as a heterogeneous and Brønsted acid catalyst under solvent-free conditions at room temperature (Table 1). As it can be seen in Table 1, when reaction was carried out in the absence of the catalyst, after 120 min the reaction was without yield (Table 1, entry 1). The best results were achieved when 20 mol% of the BAIL was appropriate to promote the reaction efficiently and give the product in excellent yield and in short reaction time (Table 1, entry 6). Additionally, it is worth noting that when a higher percentage of loading of the BAIL was used, the yields did not improve (Table 2, entry 6).
Table 1

Result of the amount of the catalyst in the synthesis of compound 3a under solvent-free conditions

Entry

Catalyst loading (%)

Reaction time (min)

Yield (%)a

1

None

120

2

1

100

35

3

5

90

54

4

10

90

75

5

15

45

80

6

20

20

85

7

25

20

85

aYield of isolated products

Table 2

Optimization of temperature in the synthesis of compound 3a under solvent-free conditions

Entry

Temperature (°C)

Reaction time (min)

Yield (%)a

1

60

55

81

2

80

40

87

3

100

30

94

4

110

15

94

5

120

20

94

aYield of isolated products

To optimize the temperatures, the condensation of benzaldehyde (1 mmol) and 2-naphthol (2 mmol) in the presence of 20 mol% of BAIL was checked, and the results are tabulated in Table 2. As it can be seen in Table 2, temperature increase was appropriate for the synthesis of compound 3a. Therefore, the model reaction in solvent-free conditions at 110 °C leads to the highest yield (94%) and shortest reaction time (15 min) compared to the other temperatures.

In the next study, to compare the efficiency of solvent-free conditions versus solvent conditions, the condensation reaction between benzaldehyde (1 mmol) and 2-naphthol (2 mmol) using BAIL (20 mol%) was tested in various solvents such as ethanol, methanol, chloroform, dichloromethane, and ethyl acetate under reflux conditions, and the results are summarized in Table 3. As it can be seen in Table 3, low yields of the product and longer reaction time rather than solvent-free conditions were obtained. Hence, performing the reaction under solvent-free conditions and in the presence of 20 mol% of BAIL at 110 °C was determined as the optimal condition.
Table 3

Optimization of various solvents in the synthesis of compound 3a on the model reaction under reflux condition

Entry

Solvent (5 ml)

Reflux conditions (°C)

Reaction time (min)

Yield (%)a

1

EtOH

78.3

60

44

2

MeOH

65

60

40

3

CHCl3

61.2

60

51

4

CH2Cl2

39.6

60

45

5

EtOAc

77.1

60

30

aYield of isolated products

To assess the efficiency and the scope of BAIL for the synthesis of biologically active 14-aryl-14H-dibenzo[a,j]xanthene derivatives, a variety of aromatic aldehydes (containing electron-withdrawing, electron-donating groups, and halogens on their aromatic ring) were reacted with 2-naphthol in the optimal reaction conditions to produce the desired products 3ap in excellent yields and in short reaction time (Table 4). As it can be seen in Table 4, in all cases, aromatic aldehydes 3ap containing both electron-donating and electron-withdrawing groups (–NO2, –Me, –OMe, –Br, –Cl, –OH, –NR2) reacted with 2-naphthol under solvent-free conditions at 110 °C for an appropriate time (10–30 min) and good to excellent yields (81–95%) to generate 14-aryl-14H-dibenzo[a,j]xanthene derivatives.
Table 4

The solvent-free synthesis of biologically active 14-aryl-14H-dibenzo[a,j]xanthene derivatives using silica supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride

Entry

Aldehydes

Time (min)a

Yield (%)b

M.p. °C (Lit)

Found

Reported

3a

C6H5

15

94

188–190

191–193 [34]

3b

2-NO2C6H4

30

84

308–310

309–311 [34]

3c

3-NO2C6H4

30

89

211–213

210–212 [34]

3d

3-OCH3C6H4

12

90

261–263

260–262 [34]

3e

4-BrC6H4

25

94

295–296

294–295 [34]

3f

4-CH3C6H4

20

88

225–227

226–228 [34]

3g

4-OCH3C6H4

15

85

201–203

203–205 [34]

3h

4-ClC6H4

10

93

282–284

285–287 [34]

3i

4-NO2C6H4

20

95

309–311

310–312 [34]

3j

3-OHC6H4

25

84

171–173

169–171 [34]

3k

4-OHC6H4

22

87

140–141

1387–139 [34]

3l

2-ClC6H4

17

85

221

219–220 [34]

3m

2,4-ClC6H3

13

95

86–88

87–89 [34]

3n

4-C6H5C6H4

30

81

279–281

281–283 [34]

3o

2,3-ClC6H3

15

94

220–222

221–224 [48]

3p

4-N,N-(CH3)2C6H4

30

90

222–224

224–226 [49]

aReactions were run till the completion as indicated by TLC

bYield of isolated products

The recovery and reusability of the catalyst is a very important factor in industry and green chemistry, and also one of the advantages of heterogeneous catalyst. It is also worth noting that silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a catalyst can be recovered at the end of the reaction and can be used six times without losing its activity (Fig. 5). The yields of 4-(4-nitrophenyl)-14H-dibenzo[a,j]xanthenes 3i obtained after 15 min include 95, 93, 93, 91, 91 and 88%, respectively.
Fig. 5

Recyclability of the SiO2/[SEP]Cl for the synthesis of compound 3i after 15 min

The advantages of BAIL were compared (solvent, catalyst loading, time, yield, and temperature) with some other catalysts for the synthesis of compound 3a from the reaction between benzaldehyde with 2-naphthol, and the results are represented in Table 5. In 2012, Rao et al. (Table 5, entry 3) reported the preparation of 14-aryl-14H-dibenzo[a,j]xanthenes using ZnO NPs; in this procedure, the yield of products are low (80%) and reaction time is long (60 min). On the other hand, this procedure needs high temperature (150 °C) to complete the reaction. In 2008, Khaksar et al. (Table 5, entry 5) reported a highly efficient method for the synthesis of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthenes using pentafluorophenyl ammonium triflate (PFPAT); this method relies on the use of toxic solvent like toluene, and requires very long reaction time (4.5 h). In addition, one of the other problems is that the catalyst used in this method is non-recyclable. Recently, Kumara et al. in 2006 reported the use of Selectfluor™ (Table 5, entry 7) as a catalyst for the preparation of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene derivatives in which the reaction completion time was very long and tedious (8 h), and also requires high temperature (125 °C). Wang et al. in 2009 reported the use of iodine (Table 5, entry 9) as a catalyst for the synthesis of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene derivatives under neat conditions; one of the main problems of this method is the use of iodine, which is toxic and biodegradable, and the reaction time is long. As it can be seen in Table 5, the reaction in the presence of BAIL was simpler, solvent free, economical, eco-friendly, the catalyst used was recyclable, and the reaction time was shorter. On the whole, it seems that this catalytic system can be an appropriate alternative method for the synthesis.
Table 5

Comparison of various catalysts used for the synthesis of compound 3a

Entry

Reaction condition

Time (h)

Yield (%)a

Refs.

1

Silica sulfuric acid (0.05 g)/solvent free/125 °C

20b

90

[33]

2

Yb(OTf)3/[BPy]BF4 (0.01 mmol)/110 °C

7

89

[37]

3

ZnO NPs (0.3 mmol)/solvent free/150 °C

60b

80

[43]

4

PVPP-BF3/solvent free (0.05 g)/120 °C

1.5

94

[31]

5

PFPAT (10 mol%)/toluene/25–30 °C

4.5

90

[32]

6

H5PW10V2O40 (0.5 mol%)/solvent-free/100 °C

1

67

[35]

7

Selectfluor™ (0.1 m mol)/neat conditions/125 °C

8

93

[40]

8

Polytungstozincate acid (0.05 g)/solvent free/80 °C

1

81

[46]

9

Iodine (0.1 mmol)/neat conditions/90 °C

2.5

90

[42]

10

SiO2/[SEP]Cl (20 mol%)/solvent free/110 °C

15b

94

aYield of isolated products

bIn minute

Conclusion

In summary, silica-supported 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO2/[SEP]Cl as a new and recoverable heterogeneous catalyst was employed for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives by the one-pot condensation reaction of various aldehydes with 2-naphthol under thermal and solvent-free conditions. This methodology offers very attractive features such as economic viability of catalyst, short reaction time, high yield of products, operational simplicity, easier workup procedure, ease of recovering and reusing of the catalyst, and higher turn-over frequency of the catalyst in comparison to previously reported catalysts.

Notes

Acknowledgements

The authors gratefully acknowledge partial support of this study by the Payame Noor University (PNU) of Ilam, I.R. Iran.

References

  1. 1.
    Li TS, Zhang ZH, Yang F, Fu CG (1998) Montmorillonite clay catalysis. Part 7. 1 an environmentally friendly procedure for the synthesis of coumarins via pechmann condensation of phenols with ethyl acetoacetate. J Chem Res 1:38–39CrossRefGoogle Scholar
  2. 2.
    Ngo HL, LeCompte K, Hargens L, McEwen AB (2000) Thermal analysis of polyethylene graft copolymers. Thermochim Acta 97:357–361Google Scholar
  3. 3.
    Zhao D, Wu M, Kou Y, Min E (2002) Ionic liquids: applications in catalysis. Catal Today 74:157–189Google Scholar
  4. 4.
    Sheldon RA, Maderia-Lau L, Sorgedrager MJ, Van Rantwijk F, Seddon KR (2002) Biocatalysis in ionic liquids. Green Chem 4:147–151CrossRefGoogle Scholar
  5. 5.
    Yang C, Sun Q, Qiao J, Li Y (2003) Ionic liquid doped polymer light-emitting electrochemical cells. J Phys Chem B 107:12981–12988CrossRefGoogle Scholar
  6. 6.
    Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellose with ionic liquids. J Am Chem Soc 124:4974–4975CrossRefGoogle Scholar
  7. 7.
    Zhang S, Zhang Q, Zhang ZC (2004) Extractive desulfurization and denitrogenation of fuels using ionic liquids. Ind Eng Chem Res 43:614–622CrossRefGoogle Scholar
  8. 8.
    Vygodskii YS, Shaplov AS, Lozinskaya EI, Filippov OA, Shubina ES, Bandari R, Buchmeiser MR (2006) Ring-Opening Metathesis Polymerization (ROMP) in ionic liquids: scope and limitations. Macromolecules 39:7821–7830CrossRefGoogle Scholar
  9. 9.
    Liu ZM, Sun SY, Han BX, Zhang JL, Huang J, Du JM, Miao SD (2006) Microwave-assisted synthesis of Pt nanocrystals and deposition on carbon nanotubes in ionic liquids. J Nanosci Nanotechnol 6:175–179Google Scholar
  10. 10.
    Swatloski RP, Visser AE, Reichert WM, Broker GA, Facina LM, Holbrey JD, Rogers RD (2002) On the solubilization of water with ethanol in hydrophobic hexafluorophosphate ionic liquids. Green Chem 4:81–87CrossRefGoogle Scholar
  11. 11.
    Nishiyama T, Sakita K, Fuchigami T, Fukui T (1998) Antioxidant activities of fused heterocyclic compounds, xanthene-2,7-diols with BHT or catechol skeleton. Polym Degrad Stab 62:529–534CrossRefGoogle Scholar
  12. 12.
    Bhattacharya AK, Rana KC, Mujahid M, Sehar I, Saxena AK (2009) Synthesis and in vitro study of 14aryl-14H-dibenzo[a, j]xanthenes as cytotoxic agents. Bioorg Med Chem Lett 19:5590–5593CrossRefGoogle Scholar
  13. 13.
    Bhattacharya AK, Rana KC, Mujahid M, Sehar I, Saxena AK (2009) Synthesis and in vitro study of 14-aryl-14H-dibenzo[a.j]xanthenes as cytotoxic agents. Bioorg Med Chem Lett 19:5590–5593CrossRefGoogle Scholar
  14. 14.
    Kumar A, Sharma S, Maurya RA, Sarkar JJ (2010) Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity. Comb Chem 12:20–24CrossRefGoogle Scholar
  15. 15.
    Omolo JJ, Johnson MM, Van Vuuren SF, de Koning CB (2011) The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity. Bioorg Med Chem Lett 21:7085–7088CrossRefGoogle Scholar
  16. 16.
    Chibale K, Visser M, Schalkwyk DV, Smith PJ, Saravanamuthu A, Fairlamb AH (2003) Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents. Tetrahedron 59:2289–2296CrossRefGoogle Scholar
  17. 17.
    El-Brashy AM, El-Sayed Metwally M, El-Sepai FA (2004) Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes. Farmaco 59:809–817CrossRefGoogle Scholar
  18. 18.
    Ahmad M, King TA, Ko DK, Cha BH, Lee J (2002) Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases. J Phys D Appl Phys 35:1473–1476CrossRefGoogle Scholar
  19. 19.
    Knight CG, Stephens T (1989) Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. studies in phospholipid vesicles. Biochem J 258:683–687CrossRefGoogle Scholar
  20. 20.
    Sharma GD, Balraju P, Kumar M, Roy MS (2009) Quasi solid state dye sensitized solar cells employing a polymer electrolyte and xanthene dyes. Mater Sci Eng B 162:32–39CrossRefGoogle Scholar
  21. 21.
    Chang CC, Yang YT, Yang JC, Wu HD, Tsai T (2008) Absorption and emission spectral shifts of rose bengal associated with DMPC liposomes. Dyes Pigment 79:170–175CrossRefGoogle Scholar
  22. 22.
    Chu ZZ, Wang D, Zhang C, Wang FH, Wu HW, Lv ZB, Hou SC, Fan X, Zou DC (2012) Synthesis of spiro[fluorene-9,9′-xanthene] derivatives and their application as hole-transporting materials for organic light-emitting devices. Synth Met 162:614–620CrossRefGoogle Scholar
  23. 23.
    Qi H, Zhu BW, Abe N, Shin Y, Murata Y, Nakamura Y (2012) Involvement of intracellular oxidative stress-sensitive pathway in phloxine B-induced photocytotoxicity in human Tlymphocytic leukemia cells. Food Chem Toxicol 50:1841–1847CrossRefGoogle Scholar
  24. 24.
    Thangadurai D, Ramesh N, Viswanathan MB, Prasad DX (2001) A novel xanthene from Indigofera longeracemosa stem. Fitoterapia 72:92–94CrossRefGoogle Scholar
  25. 25.
    Huang L, Lei T, Lin CW, Kuang XC, Chen HY, Zhou H (2010) Blumeaxanthene II, a novel xanthene from Blumea riparia DC. Fitoterapia 81:389–392CrossRefGoogle Scholar
  26. 26.
    Knignt DW, Little PB (1998) The first high-yielding benzyne cyclisation using a phenolic nucleophile: a new route to xanthenes. Synlett 1998:1141–1143CrossRefGoogle Scholar
  27. 27.
    Wang JQ, Harvey GR (2002) Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters. Tetrahedron 58:5927–5931CrossRefGoogle Scholar
  28. 28.
    Casiraghi G, Casnati G, Cornia M (1973) Regiospecific reactions of phenol salts: reaction-pathways of alkylphenoxy-magnesiumhalides with triethylorthoformate. Tetrahedron Lett 14:679–682CrossRefGoogle Scholar
  29. 29.
    Kuo CW, Fang JM (2001) Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl–carbonyl couplings reactions. Synth Commun 31:877–892CrossRefGoogle Scholar
  30. 30.
    Khoeiniha R, Ezabadi A, Olyaei A (2016) An efficient solvent-free synthesis of 1,8-dioxo-octahydroxanthenes by using Fe2(SO4)3.7H2O as catalyst. Iran Chem Commun 4:237–282Google Scholar
  31. 31.
    Mokhtary M, Refahati S (2013) Polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF3): mild and efficient catalyst for the synthesis of 14-aryl-14H-dibenzo [a, j] xanthenes and bis(naphthalen-2-yl-sulfane) derivatives. Dyes Pigm 99:378–381CrossRefGoogle Scholar
  32. 32.
    Khaksar S, Behzadi N (2012) Mild and highly efficient method for synthesis of 14-aryl(alkyl)-14H-dibenzo[a, j]xanthenes and 1,8-Dioxooctahydroxanthene derivatives using pentafluorophenyl ammonium triflate as a novel organocatalyst. Chin J Catal 33:982–985CrossRefGoogle Scholar
  33. 33.
    Shaterian HR, Ghashang M, Hassankhani A (2008) One-pot synthesis of aryl 14H-dibenzo[a, j]xanthene leuco-dye derivatives. Dyes Pigment 76:564–568CrossRefGoogle Scholar
  34. 34.
    Haeri HS, Rezayati S, Rezaee Nezhad E, Darvishi H (2016) Fe2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles: efficient and recyclable green catalyst for the synthesis of 14-aryl-14H-dibenzo[a, j]xanthene derivatives. Res Chem Intermed 42:4773–4784CrossRefGoogle Scholar
  35. 35.
    Tayebee R, Tizabi Sh (2012) Highly efficient and environmentally friendly preparation of 14-aryl-14H dibenzo[a, j]xanthenes catalyzed by tungsto-divanado-phosphoric acid. Chin J Catal 33:962–969CrossRefGoogle Scholar
  36. 36.
    Venu-Madhav J, Thirupathi-Reddy Y, Narsimha-Reddy P (2009) Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions. J Mol Catal A Chem 304:85–87CrossRefGoogle Scholar
  37. 37.
    Su W, Yang D, Jin C, Zhang B (2008) 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 49:3391–3394CrossRefGoogle Scholar
  38. 38.
    Rezayati S, Seifournia H, Mirzajanzadeh E (2017) 2,6-Pyridinedicarboxylic acid as an efficient and mild organocatalyst for the one-pot synthesis of xanthene derivative. Asian J Green Chem 1:24–33CrossRefGoogle Scholar
  39. 39.
    Sajjadifar S, Fadaeian M, Bakhtiyari M, Rezayati S (2014) One-pot synthesis of xanthene derivatives using silica supported [2-(sulfooxy)ethyl]sulfamic acid as a novel and efficient catalyst under solvent-free condition. Chem Sci Trans 3:107–116Google Scholar
  40. 40.
    Kumara PS, Sunil Kumara B, Rajithaa B, Narsimha Reddya P, Sreenivasulua N, Thirupathi Reddy Y (2006) A novel one pot synthesis of 14-aryl-14H-dibenzo[a, j]xanthenes catalyzed by selectfluorTM under solvent free conditions. Arkivoc 2006(XII):46–50Google Scholar
  41. 41.
    Mirkhani V, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I, Mahdavi M (2009) Highly efficient synthesis of 14-Aryl-14H-dibenzo[a, j]xanthenes catalyzed by carbon-based solid acid under solvent-free conditions. Synth Commun 39:4328–4340CrossRefGoogle Scholar
  42. 42.
    Wang RZ, Zhang LF, Cui ZS (2009) Iodine-catalyzed synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one derivatives via multicomponent reaction. Synth Commun 39:2101–2107CrossRefGoogle Scholar
  43. 43.
    Rao GBD, Kaushik MP, Halve AK (2012) An efficient synthesis of naphtha[1,2-e]oxazinone and 14-substituted-14H-dibenzo[a, j]xanthene derivatives promoted by zinc oxide nanoparticle under thermal and solvent-free conditions. Tetrahedron Lett 53:2741–2744CrossRefGoogle Scholar
  44. 44.
    Khurana JM, Magoo D (2009) 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 50:4777–4780CrossRefGoogle Scholar
  45. 45.
    Khazaei A, Zolfigol MA, Moosavi-Zare AR, Zare A, Khojasteh M, Asgari Z, Khakyzadeh V, Khalafi-Nezhad A (2012) 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 20:54–57CrossRefGoogle Scholar
  46. 46.
    Mohammadpour Amini M, Fazaeli Y, Yassaee Z, Feizi Sh, Bazgir A (2009) Polytungstozincate acid: a new and efficient catalyst for the synthesis of xanthenes under solvent-free conditions. Open Catal J 2:40–44CrossRefGoogle Scholar
  47. 47.
    Klass DL (1964) Addition of sulfur trioxide—pyridine to aldehydes. J Org Chem 29:2666–2669CrossRefGoogle Scholar
  48. 48.
    Moosavi-Zare AR, Zolfigol MA, Zarei M, Zare A, Khakyzadeh V (2015) Application of silica-bonded imidazolium-sulfonic acid chloride (SBISAC) as a heterogeneous nanocatalyst for the domino condensation of arylaldehydes with 2-naphthol and dimedone. J Mol Liq 211:373–380CrossRefGoogle Scholar
  49. 49.
    Shaterian HR, Hosseinian A, Ghashang M (2009) Ferric hydrogen sulfate as an efficient heterogeneous catalyst for environmentally friendly greener synthesis of 1,8-dioxo-octahydroxanthenes. Turk J Chem 33:233–240Google Scholar

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Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran

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