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Original article
12 (
7
); 1515-1521
doi:
10.1016/j.arabjc.2014.10.026

Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in water

, , ,
a Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran
b Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65178, Hamedan, Iran
c Young Researchers Club, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran

⁎Corresponding author. Fax: +98 11 42517087. m.vahdat@iauamol.ac.ir (Seyed Mohammad Vahdat) vahdat_mohammad@yahoo.com (Seyed Mohammad Vahdat)

Received: , Accepted: ,
© The Author(s) 2016
Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

Graphical abstract

Abstract

In the present study, we introduce two nonconventional ionic liquids [MIMPS]3PW12O40 (a) and [TEAPS]3PW12O40 (b) as green and highly efficient solid acid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives. The one-pot three component reaction of 1,3-cyclohexanediones, aromatic aldehydes and aromatic amines or ammonium acetate in water afforded the corresponding 1,8-dioxo-decahydroacridines in excellent yields. This reaction has been carried out in the presence of 1 mol% of catalysts at room temperature. The reusability of the catalysts was demonstrated by a five-run test. Additionally, the catalysts pose several advantages including mild reaction conditions, cleaner reactions and shorter reaction times.

Keywords

Ionic liquid
Green solid acid catalyst
1,8-Dioxo-decahydroacridine
One-pot synthesis
Water solvent
1

1 Introduction

Acridine and acridine-1,8-dione derivatives are polyfunctionalized 1,4-dihydropyridine derivatives. They have a wide range of pharmacological properties such as antimalaria (Spalding et al., 1954), antitumor (Mikata et al., 1998), anticarcinogenic (Lacassagne et al., 1956), anticancer (Gamega et al., 1999), fungicidal (Wainwright, 2001), cytotoxic (Antonini et al., 1999), anti-multidrug-resistant (Gallo et al., 2003), antimicrobial (Ngadi et al., 1990) and widely prescribed as calcium b-blockers (Bossert and Vater, 1989; Berkan et al., 2002). Also, 1,8-dioxo-decahydroacridines were created to act as laser dyes (Murugan et al., 1998; Islam et al., 2003) and used as photoinitiators (Tu et al., 2004).

Many procedures explained the synthesis of acridine derivatives containing 1,4-dihydropyridines, from dimedone, aldehydes and different nitrogen sources such as urea (Bakibaev et al., 1991), hydroxylamine (Fang et al., 2004), ammonium acetate on basic alumina (Suárez et al., 1999), ammonium bicarbonate (Tu et al., 2002), ammonium hydroxide and different appropriate amines or ammonium acetate (Martin et al., 1995), via conventional heating in organic solvents, in the presence of Amberlyst-15 (Das et al., 2006), p-dodecylbenzenesulfonic acid (DBSA) (Jin et al., 2004), triethylbenzylammonium chloride (TEBAC) (Wang et al., 2004), Zn(OAc)2·2H2O or ammonium chloride or L-proline (Balalaie et al., 2009), Proline (Venkatesan et al., 2009), under microwave irradiation (Miao et al., 2002; Wang et al., 2003), and using ionic liquids (li et al., 2005; Zhang et al., 2006), such as bronsted acidic imidazolium salts containing perfluoroalkyl tails (Shen et al., 2009), 1-methylimidazolium trifluoroacetate ([Hmim]TFA) (Dabiri et al., 2008).

However, some of these reported methods have one or more disadvantages such as moisture sensitive, using the excess of catalysts, prolonged reaction time, low yields, toxic organic solvents, a microwave oven and unpleasant experimental procedure and reagents which are expensive. Performing organic reactions in aqueous media has attracted much attention because of wonderful water properties. It would be significantly safe, cheap, non-toxic and environmentally friendly compared to organic solvents (Li and Chan, 1997). Additionally, the catalyst system can be recycled using the water soluble catalyst and the insoluble products can be separated by simple filtration. So, development of a mild and efficient catalyst system for the synthesis of 1,8-dioxo-decahydroacridines is highly desirable. It should not only be stable in water but also should be completely soluble in it.

In recent years, ionic liquids have attracted much attention as a new class of green solvents and catalysts (Khalafi-Nezhad and Mokhtari, 2004). These aqueous media is utilized for organic synthesis due to their astonishing properties, such as wide liquid range, favorable solvating capability, low temperature requirement, tunable polarity, high thermal stability, and ease of recyclability (Welton, 1999, 2004; Wasserscheid and Keim, 2000). Ionic liquids also have negligible vapor pressure, which facilitates product separation by distillation. Moreover, they are the cheapest and most environmentally friendly solvents, because water exhibits unique reactivity and selectivity, which differs from those in conventional organic solvents. The appropriate property of the ionic liquids leads to the development and application of so-called “task-specific” ionic liquids to synthesize the desirable products. Recently, Wang et al. (2009) prepared new heteropolyanion-based ionic liquids containing the acidic functional group as ‘‘task-specific’’ catalysts (a,b), (Scheme 1).

Ionic liquids’ (a,b) Structure applied in this study.
Scheme 1 Ionic liquids’ (a,b) Structure applied in this study.

In the present research, we report two green solid catalysts for the synthesis of 1,8-dioxo-decahydroacridine derivatives in aqueous media by the one-pot three component reaction of 1,3-cyclohexanediones, aromatic aldehydes and aromatic amines or ammonium acetate. They pose much higher activity in comparison with the other reported catalysts as well as the additional advantage of reusability. Remarkably, the conventional ionic liquids (ILs) maintain their liquid state at room temperature or to some extent higher (20–30 °C). However, the catalysts used here (a,b) exhibit some different and noteworthy properties compared to the other room temperature ionic liquids (RTILs) because of the high value of melting point (above 100 °C). They revealed to be highly efficient green and homogeneous catalysts because of their good solubility in water. Also, the catalyst offers several advantages including mild reaction conditions, shorter reaction times, cleaner reactions, high yield of the products, simply recovered and fairly steadily reused, lower catalytic loading as well as simple experimental and isolation procedures which make it useful for the synthesis of 1,8-dioxo-decahydroacridines.

2

2 Results and discussion

First, we studied three-component condensation of dimedone (2 mmol), 4-chlorobenzaldehyde (1 mmol) and p-toluidine (1 mmol) to optimize the reaction conditions with respect to temperature, time, solvent, molar ratio of catalyst to the substrate and reusability of catalyst. It was found that 1 mol% of catalyst was sufficient to obtain the desired 1,8-dioxo-decahydroacridines in 96% yield within 21 min at room temperature in water (Scheme 2).

Synthesis of 1,8-dioxo-decahydroacridines under condition i or ii.
Scheme 2 Synthesis of 1,8-dioxo-decahydroacridines under condition i or ii.

After finding the optimized reaction conditions, the investigation was preceded by performing the reaction between a series of aromatic aldehydes and primary amines or ammonium acetate with 1,3-cyclohexanediones. To show the general applicability of this method, various aldehydes and amines were efficiently reacted with two equivalents of 1,3-cyclohexanediones in the same conditions. These results encouraged us to investigate the scope and the generality of this new protocol for various aldehydes and amines under optimized conditions. As shown in Table 1, a series of aromatic aldehydes and amines underwent electrophilic substitution reaction with 1,3-cyclohexanediones to afford a wide range of substituted 1,8-dioxo-decahydroacridines in good to excellent yields. The nature and electronic properties of the substituents on the aromatic ring affect the conversion rate, and aromatic aldehydes having electron-withdrawing groups on the aromatic ring (Table 1, entries 2, 9, 18, 22, 26) react faster than electron-donating groups (Table 1, entries 7, 14, 24, 32, 36). Also, both aromatic amines and ammonium acetate similarly underwent well to the conversion. Notably, the obtained results depict that the catalyst (a) has more activity than catalyst (b) which is in accordance with that of the PS bearing catalyst.

Table 1 Synthesis of 1,8-dioxo-decahydroacridines under condition i or ii.a
Entry R1 R2 Amine [MIMPS]3PW12O40 [TEAPS]3PW12O40 M.p. (°C) (Refs.)
Time (min) Yield (%)b Time (min) Yield (%)b
1 H H NH4OAc 36 91 57 88 279–280 (Kidwai and Bhatnagar, 2010)
2 H 3-NO2 NH4OAc 29 97 47 96 282–284 (Kidwai and Bhatnagar, 2010)
3 H 4-Cl NH4OAc 31 95 49 94 297–298 (Kidwai and Bhatnagar, 2010)
4 H 2-OH NH4OAc 34 91 54 91 305–306 (Kidwai and Bhatnagar, 2010)
5 H 4-OH NH4OAc 33 92 53 91 303–305 (Kidwai and Bhatnagar, 2010)
6 H 2-OMe NH4OAc 33 91 52 91 300–302 (Kidwai and Bhatnagar, 2010)
7 H 4-OMe NH4OAc 31 93 50 93 303–305 (Kidwai and Bhatnagar, 2010)
8 Me H NH4OAc 33 92 53 89 290–291 (Zhang et al., 2006)
9 Me 3-NO2 NH4OAc 23 97 40 96 307–308 (Zhang et al., 2006)
10 Me 4-Cl NH4OAc 29 95 44 93 298–300 (Kidwai and Bhatnagar, 2010)
11 Me 2-OH NH4OAc 31 92 50 91 310–311 (Kidwai and Bhatnagar, 2010)
12 Me 4-OH NH4OAc 29 93 47 91 303–305 (Kidwai and Bhatnagar, 2010)
13 Me 2-OMe NH4OAc 29 93 47 90 293–295 (Kidwai and Bhatnagar, 2010)
14 Me 4-OMe NH4OAc 27 92 46 91 276–278 (Kidwai and Bhatnagar, 2010)
15 Me 4-Me NH4OAc 27 93 44 92 278–280 (Zhang et al., 2006)
16 Me 2,3-(OMe)2 NH4OAc 26 93 45 91 325–327 (Zhang et al., 2006)
17 H H Aniline 28 92 45 91 274–276 (Venkatesan et al., 2009)
18 H 3-NO2 Aniline 21 97 36 97 278–279 (Bhatnagar and Kidwai, 2010)
19 H 4-Cl Aniline 24 96 39 96 292–293 (Bhatnagar and Kidwai, 2010)
20 H 2-OMe Aniline 26 94 42 93 270–272 (Chandrasekhar et al., 2008)
21 Me H Aniline 25 94 41 92 253–255 (Das et al., 2006)
22 Me 3-NO2 Aniline 18 98 23 97 296–297 (Bhatnagar and Kidwai, 2010)
23 Me 4-Cl Aniline 22 96 35 95 244–246 (Bhatnagar and Kidwai, 2010)
24 Me 2-OMe Aniline 23 95 35 94 219–221 (Das et al., 2006)
25 Me H p-Toluidineiline 26 93 39 92 262–264 (Jin et al., 2004)
26 Me 3-NO2 p-Toluidineiline 19 97 31 96 284–286 (Jin et al., 2004)
27 Me 3-Cl p-Toluidineiline 23 95 35 95 315–316 (Jin et al., 2004)
28 Me 4-Cl p-Toluidineiline 21 96 33 95 271–273 (Jin et al., 2004)
29 Me 2,4-(Cl)2 p-Toluidineiline 22 97 33 94 320–322 (Jin et al., 2004)
30 Me 3,4-(Cl)2 p-Toluidineiline 22 96 33 94 251–253 (Shen et al., 2009)
31 Me 4-Me p-Toluidineiline 23 95 35 95 296–298 (Shen et al., 2009)
32 Me 4-OMe p-Toluidineiline 25 93 37 92 281–283 (Jin et al., 2004)
33 Me H 4-Methoxyaniline 26 93 37 93 215–216 (Shen et al., 2009)
34 Me 4-Cl 4-methoxyaniline 20 97 33 95 251–253 (Shen et al., 2009)
35 Me 4-Me 4-Methoxyaniline 23 94 35 94 237–239 (Shen et al., 2009)
36 Me 4-OMe 4-Methoxyaniline 24 93 37 92 212–214 (Shen et al., 2009)
a Reaction condition: Aromatic aldehyde (1 mmol), 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexenedione (2 mmol), amine (1 mmol) catalyst (1 mol%), solvent (2 mL).
b Isolated yield.

The effect of solvent on the yield of 1,8-dioxo-decahydroacridines is given in Table 2. The reaction between dimedone, aniline and benzaldehyde was chosen as a model reaction for investigating the effect of solvent. From Table 2 we can know that water is obviously the best choice for these reactions. Another reason we chose water as the solvent of this reaction is that water is a green solvent.

Table 2 Solvent effect on the reaction between dimedone, aniline and benzaldehyde.a
Entry Solvent [MIMPS]3PW12O40 [TEAPS]3PW12O40
Time (min) Yield (%)b Time (min) Yield (%)b
1 H2O 25 94 41 92
2 C2H5OH 25 94 42 92
3 CH3CN 29 91 45 89
4 CH3COOC2H5 33 88 49 84
5 Toluene 37 84 53 82
6 Benzene 41 81 57 78
a Reaction condition: 5,5-dimethyl-1,3-cyclohexenedione (2 mmol), aniline (1 mmol), benzaldehyde (1 mmol), catalyst (1 mol%), solvent (2 mL).
b Isolated yield.

In order to show the merit of ILs in comparison with the other catalysts used for the similar reaction, some of the results are tabulated in Table 3. According to Table 3, the required ratio for the most catalysts used for this purpose is >1 mol% and also the required reaction times are much longer (5–6 h).

Table 3 Comparison reaction between dimedone, 4-chlorobenzaldehyde and p-toluidineiline in the presence of different catalysts.a
Entry Catalyst Catalyst (mol %) Time (min) Yield (%)b (Refs.)
1 [MIMPS]3PW12O40 1 21 96 This work
2 [TEAPS]3PW12O40 1 33 95 This work
3 PTSA 2 360 18 Dabiri et al. (2008)
4 C7H15COOH 2 360 31 Dabiri et al. (2008)
5 DBSA 2 360 41 Dabiri et al. (2008)
6 [HMIM]TFA 0.1 g 300 84 Das et al. (2006)
7 TsOH 10 360 13.2 Jin et al. (2004)
8 Sc(DS)3 10 360 78.3 Jin et al. (2004)
9 C11H15COOH 10 360 26.8 Jin et al. (2004)
a Reaction condition: Dimedone (2 mmol), aniline (1 mmol), 4-chlorobezaldehyde (1 mmol).
b Isolated yield.

So, when isophthalaldehyde (5) was used with 4 molar equivalents of 1,3-cyclohexanediones and 2 molar equivalents of aromatic amines, bisacridine-1,8-diones (6) was obtained in excellent yield (Kaya et al., 2011). The reactions were carried out fewer than two conditions and the experimental results demonstrate the higher activity of catalyst as compared to catalyst b, (Scheme 3).

Synthesis of bisacridine-1,8-diones under condition i or ii.
Scheme 3 Synthesis of bisacridine-1,8-diones under condition i or ii.

The high chemoselectivity of this reaction had also been verified by a competitive reaction between dimedone, acetophenone and aniline, as shown in Scheme 4. The result showed that aniline was carried out with dimedone in excellent yield and acetophenone observed with product under identical conditions. The high chemoselectivity of this reaction is the result of more reactivity of 1,3-diketone compared with ketone.

Chemoselectivity of aniline in the reaction with dimedone in the presence of acetophenone.
Scheme 4 Chemoselectivity of aniline in the reaction with dimedone in the presence of acetophenone.

The reusability of the catalysts is a significant advantage and makes them useful for commercial applications. The reusability of the catalysts was checked using dimedone, 4-chlorobenzaldehyde and p-toluidineiline as a model substrate. At the end of the reaction, CH2Cl2 was added to the mixture. The aqueous layer was separated and used without further purification. In this media, as shown in Table 4, the recovered catalyst can be reused at least five additional times in subsequent reactions without appreciable loss in the catalytic activity.

Table 4 Reusability studies of the catalyst for synthesis of 9-(4-chlorophenyl)-3,3,6,6-tetramethyl-10-p-tolyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (Table 1, entry 28).a
Number of experiments 1 2 3 4 6
Isolated yield-under condition i (%)b 96 96 95 94 93
Isolated yield-under condition ii (%)b 95 94 92 92 91
a Reaction condition: Dimedone (2 mmol), p-toluidineiline (1 mmol), 4-chlorobezaldehyde (1 mmol), catalyst (1 mol%), solvent (2 mL).
b Isolated yield.

3

3 Experimental

All starting materials were obtained from Merck and Fluka, and were used without further purification. Melting points were obtained on a Thermo Scientific apparatus and were not corrected. IR spectra were recorded on a FT-IR Bruker (WQF-510) spectrometer. 1H and 13C NMR spectra were recorded on a Bruker DRX-400 AVANCE spectrometer (400 and 100 MHz, respectively).

3.1

3.1 General procedure for the synthesis of 1,8-dioxodecahydroacridine derivatives

A mixture of 1,3-diketone (2.0 mmol), aromatic aldehyde (1.0 mmol), aromatic amine or ammonium acetate (1.0 mmol) and ionic liquids (1 mol%) in water (2 mL) was stirred at room temperature for an appropriate time. The progress of the reaction was monitored by TLC (n-hexane/ethyl acetate 4:1). After completion of the reaction, the resulting solid (crude product) was filtered and then recrystallized from ethanol–water to obtain pure product. The physical data (M.p., NMR, IR) of these known compounds were found to be identical with those reported in the literature.

3.2

3.2 3,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H, 5H)-dione (Table 1, entry 8)

M.p. 290–291 °C; IR spectrum (KBr), ν, cm−1: 755 (−CH out of bending of aromatic ring), 1226 (CN stretching), 1486, 1585 (C⚌C− stretching of aromatic ring), 1635 (C⚌O– of 1,3-diketone), 2960 (CH stretching of aliphatic), 3054 (–CH stretching of aromatic ring), 3745 (–NH stretching); 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz): 0.85 (s, 6H), 1.01 (s, 6H), 1.83–2.49 (m, 8H), 4.83 (s, 1H), 7.02–7.16 (m, 5H), 9.43 (br s, 1H, NH); 13C NMR spectrum (100 MHz, DMSO-d6), δ, ppm: 22.1, 26.4, 29.1, 30.2, 30.5, 30.9, 32.3, 32.7, 50.1, 111.4, 114.2, 123.2, 125.1, 126.7, 127.3, 127.7, 146.5, 149.3, 194.1.

3.3

3.3 9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H, 5H)-dione (Table 1, entry 23)

M.p. 244–246 °C; IR spectrum (KBr), ν, cm−1: 835 (–CH out of bending of aromatic ring), 1247 (CN stretching), 1365, 1587 (C⚌C– stretching of aromatic ring), 1633 (C⚌O– of 1,3-diketone), 2955 (CH stretching of aliphatic), 3055 (−CH stretching of aromatic ring), 3745 (–NH stretching); 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz): 0.83 (s, 6H), 0.95 (s, 6H), 1.80–2.23 (m, 8H), 5.21 (s, 1H), 7.22–7.27 (m, 4H), 7.38–7.58 (m, 5H); 13C NMR spectrum (100 MHz, DMSO-d6), δ, ppm: 22.1, 26.7, 29.5, 31.2, 32.3, 32.2, 38.1, 41.8, 50.1, 53.7, 59.6, 114.1, 115.3, 119.3, 128.1, 129.3, 129.4, 129.7, 131.3, 138.8, 144.6, 149.8, 195.5.

3.4

3.4 9,9′-(1,3-Phenylene)-bis-(10-(3-methoxyphenyl)-3,4,6,7-tetrahydroacridine-1,8-(2H, 5H, 9H, 10H)-dione) (Scheme 3, entry 1)

M.p. 258–259 °C; IR spectrum (KBr), ν, cm−1: 835 (–CH out of bending of aromatic ring), 1229 (CN stretching), 1574, 1365 (C⚌C– stretching of aromatic ring), 1637 (C⚌O– of 1,3-diketone), 2941 (CH stretching of aliphatic), 3053 (–CH stretching of aromatic ring); 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz): 1.74–1.91 (m, 4H, 2 * CH2), 1.925–2.13 (m, 4H, 2 * CH2), 2.21–2.43 (m, 12H, 6 * CH2), 2.48–2.55 (m, 2H, CH2), 2.71–2.75 (m, 2H, CH2), 3.87 (s, 6H, 2 * OCH3), 4.83 and 5.34 (2 * d, 2H, J = 18.6 Hz, CH), 6.72–6.82 (m, 4H, ArH), 7.05–7.23 (m, 6H, ArH), 7.40–7.53 (m, 2H, ArH).

3.5

3.5 9,9′-(1,3-Phenylene)-bis-(10-(2-methoxyphenyl)-3,4,6,7-tetrahydroacridine-1,8-(2H, 5H, 9H, 10H)-dione) (Scheme 3, entry 3)

M.p. 165–166 °C; IR spectrum (KBr), ν, cm−1: 785 (–CH out of bending of aromatic ring), 1230 (CN stretching), 1574, 1375 (C⚌C– stretching of aromatic ring), 1634 (C⚌O– of 1,3-diketone), 2945 (CH stretching of aliphatic), 3065 (–CH stretching of aromatic ring); 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz): 1.63–1.98 (m, 8H, 4 * CH2), 2.05–2.33 (m, 12H, 6 * CH2), 2.51–2.54 (m, 2H, CH2), 2.64–2.68 (m, 2H, CH2), 3.93 (s, 6H, 2 * OCH3), 4.54 and 5.15 (d, 2H, J = 15.7 Hz, 2 * CH), 6.52–6.76 (m, 2H, ArH), 6.93–7.15 (m, 5H, ArH), 7.22–7.51 (m, 5H, ArH).

4

4 Conclusion

In summary, two nonconventional ionic liquids (a,b) were used as an efficient catalyst for the synthesis of 1,8-dioxo-decahydroacridines which resulted to better yields. Ionic liquids effectively catalysis the one-pot three-component condensation of 1,3-cyclohexanediones, aromatic aldehydes and aromatic amines or ammonium acetate in water to produce 1,8-dioxo-decahydroacridines in excellent yields. The catalyst offers several advantages including mild reaction conditions, cleaner reactions, shorter reaction times, high yield of the products, lower catalytic loading, high melting point, green solid acid catalyst as well as simple experimental and isolation procedures. Also, the catalysts were able to be reused easily for five-time experiments with a small decrease in the catalytic activity of the recovered catalyst.

Acknowledgment

The authors are thankful for the facilities provided to carry out research in chemistry research laboratory at Ayatollah Amoli Branch, Islamic Azad University.

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