Synthesis of FAU zeolite nanoparticles as heterogeneous catalyst for one-pot synthesis of 2-substituted Aryl (Indolyl) Kojic acid derivatives under solvent-free condition

Article abstract of DOI:10.1080/15533174.2013.818019

FAU zeolite nanoparticles have been found to be a highly efficient and versatile catalyst for preparation of 2-substituted aryl (indolyl) kojic acid derivatives through one-pot condensation of kojic acid with aryl aldehydes and indoles under solvent-free

Full text of DOI:10.1080/15533174.2013.818019

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Synthesis of FAU Zeolite Nanoparticles as
Heterogeneous Catalyst for One-Pot Synthesis of 2-
Substituted Aryl (Indolyl) Kojic Acid Derivatives under
Solvent-Free Condition
Bahareh Sadeghia, Zahra Lasemib, Fereshteh Amiri Tavasolia, Saeedeh Hashemiana & Hesam
Zahedia
a Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, I. R., Iran
b Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh, I. R.,
Iran
Accepted author version posted online: 23 Jan 2014.Published online: 02 Jun 2014.
To cite this article: Bahareh Sadeghi, Zahra Lasemi, Fereshteh Amiri Tavasoli, Saeedeh Hashemian & Hesam Zahedi (2014)
Synthesis of FAU Zeolite Nanoparticles as Heterogeneous Catalyst for One-Pot Synthesis of 2-Substituted Aryl (Indolyl)
Kojic Acid Derivatives under Solvent-Free Condition, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal
Chemistry, 44:10, 1497-1503, DOI: 10.1080/15533174.2013.818019
To link to this article: http://dx.doi.org/10.1080/15533174.2013.818019
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:1497–1503, 2014
Copyright ꢀ Taylor & Francis Group, LLC
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.818019
Synthesis of FAU Zeolite Nanoparticles as Heterogeneous
Catalyst for One-Pot Synthesis of 2-Substituted Aryl (Indolyl)
Kojic Acid Derivatives under Solvent-Free Condition
Bahareh Sadeghi,1 Zahra Lasemi,2 Fereshteh Amiri Tavasoli,1 Saeedeh
Hashemian,1 and Hesam Zahedi1
1Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, I. R., Iran
2Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh, I. R., Iran
Heterogeneous catalysts have gained much importance in
recent years due to economic and environmental benefits.[10]
These catalysts are generally inexpensive and easily available.
They can conveniently be handled and removed from the re-
action mixture, thus making the experimental procedure simple
and eco-friendly. Zeolites are especially promising in their appli-
cation as heterogeneous catalysts, due to their ordered structure
and high porosity.[11,12] In this regard, we decided to use FAU
zeolite nanoparticles as a catalyst for preparing this group of
compounds.
FAU zeolite nanoparticles have been found to be a highly ef-
ficient and versatile catalyst for preparation of 2-substituted aryl
(indolyl) kojic acid derivatives through one-pot condensation of
kojic acid with aryl aldehydes and indoles under solvent-free con-
ditions. The corresponding products were obtained in very high
yields and in short reaction times.
Keywords aldehyde, FAU zeolite nanoparticles, heterogeneous cat-
alyst, indole, kojic acid, solvent-free
In this article, in continuation of our investigations of the
application of solid acids in organic synthesis,[13–19] we prepared
FAU zeolite nanoparticles and applied for the one-pot synthesis
of 2-substituted aryl (indolyl) kojic acid derivatives from kojic
acid, aryl aldehydes, and indole derivatives under solvent-free
conditions at 110◦C (Scheme 1).
INTRODUCTION
The 3-substituted indoles are important classes of organic
compounds of a large number of naturally occurring, as well as
synthetic derivatives, and occupy a prominent position in medic-
inal chemistry.[1,2] A number of 3-substituted indole derivatives
possess wide range of biological activities and pharmacological
properties, such as anticancer, antitumor,[3] antiinflammatory, EXPERIMENTAL
hypoglycemic, analgesic, and antipyretic activities.[4]
Melting points were determined with an Electrothermal 9100
On the other hand, the syntheses of kojic acid deriva-
tives have attracted great interest because of its accessibil-
ity, potential biological activity, and high reactivity.[5,6] Many
kinds of kojic acids have been prepared for biological as-
say.[7,8] Due to the vast medicinal utility of kojic acid and 3-
substituted indole derivatives, the introduction of a mild, effi-
cient, and selective method to synthesize these compounds is
still needed. There is only few articles in the literature deal-
ing with the synthesis of 2-substituted aryl (indolyl) kojic acid
derivatives.[9]
apparatus. The NMR spectra were recorded in (D6) DMSO and
CDCl3 on Bruker Avance III 400 MHz spectrometer. Elemental
analyses were determined on a CHN Elemental Analyzer LECO
600. XRD patterns were recorded by a PW3719 Instrument.
The morphologies of the products were observed using TEM
of EM10C and SEM of a XL30 Philips microscope. Materials
were purchased from Fluka and Merck companies.
Preparation of FAU Zeolite Nanoparticles
NaOH (4.07 g) and sodium aluminate (2.09 g) were dissolved
in distilled water (19.95 mL), in which meta silicate (22.07 g)
was added after 30 min. The resulting mixture was stirred 10 min
until a white gel was formed (solution A). Separately, sodium
aluminate (13.09 g) was added to a solution of NaOH (0.14 g)
in water (130.97 mL). Then meta silicate (142.43 g) was added
to this solution. The resulting mixture was stirred until a white
gel was formed (solution B). Mixing of solutions A and B under
stirring was resulted in white gel. In order to assure the formation
of white gel, the solutions were typically stirred for 24 h at room
Received 18 April 2013; accepted 11 June 2013.
We gratefully acknowledge financial support from the Research
Council of Islamic Azad University of Yazd and Islamic Azad Univer-
sity of firoozkooh of Iran.
Address correspondence to Bahareh Sadeghi, Department of Chem-
istry, Yazd Branch, Islamic Azad University, P.O. Box 89195-155,
Yazd, Iran. E-mail: sadeghi@iauyazd.ac.ir
1497

1498
B. SADEGHI ET AL.
ArCHO
2a-j
Ar
O
R'
R'
O
O
OH
+
OH
FAU Zeolite
Solvent free
HO
N
H
R
R
HO
110 oC
N
H
O
1
4a-p
3a-e
SCH. 1. Synthesis of 2-substituted aryl (indolyl) kojic acid derivatives by the reaction of kojic acid with aryl aldehyde and indole derivatives by FAU zeolite
nanoparticles
FIG. 1. FT-IR spectra of FAU zeolite nanoparticles.
FIG. 2. XRD pattern of the FAU zeolite nanoparticles.

SYNTHESIS OF FAU ZEOLITE NANOPARTICLES CATALYST
1499
FIG. 4. TEM image of the FAU zeolite nanoparticles.
FIG. 3. SEM image of the FAU zeolite nanoparticles.
Spectral Data of New Products
2-((1H-Indol-3-yl)(4-methylphenyl)methyl)-3-hydroxy-6-
1
(hydroxymethyl)-4H-pyran-4-one (4c): H NMR (400 MHz,
temperature. Then, resulting gel transferred into an autoclave,
where the hydrothermal crystallization was carried out at 100◦C
for 8 h. Finally, FAU zeolites were filtered and washed with
distilled water. This procedure was repeated until the pH of the
supernatant decreased to lower than 8. Then the powder was
dried at 110◦C over night. The as-synthesized zeolitic powders
were calcined in oven at 230◦C for 4 h.
DMSO-d6 + CDCl3, 1:4): δ 2.32 (s, 3H), 4.21 (dd, 2H), 5.65
(s, 1H), 6.29 (s, 1H), 6.63 (s, 1H), 6.70–7.35 (m, 8H), 7.43 (s,
1H), 10.19 (s, 1H). 13C NMR (100 MHz, CDCl3): δ 21.7, 38.5,
59.1, 111.3, 119.1, 119.4, 119.7, 122.1, 123.6, 126.2, 129.8,
131.4, 133.6, 134.9, 136.6, 138.7, 145.5, 150.1, 167.2, 173.3.
Anal. Calc. for C22H19O4N: C, 73.12; H, 5.30; N, 3.87. Found:
C, 73.08; H, 5.32; N, 3.80.
2-((1H-Indol-3-yl)(4-bromophenyl)methyl)-3-hydroxy-6-
(hydroxymethyl)-4H-pyran-4-one (4d): H NMR (400 MHz,
1
General Procedure for the Preparation of 2-Substituted
Aryl (Indolyl) Kojic Acid Derivatives (4)
DMSO-d6 + CDCl3, 1:4): δ 4.25 (dd, 2H), 5.57 (s, 1H), 6.19
(s, 1H), 6.67 (s, 1H), 7.03 (t, J = 8 Hz, 1H), 7.18–7.26 (m, 2H),
7.37–7.43 (m, 3H), 7.54–7.58 (m, 2H), 7.98 (s, 1H,), 10.14
(s, 1H). 13C NMR (100 MHz, CDCl3): δ 39.6, 59.2, 111.1,
119.1, 119.4, 119.8, 122.1, 123.6, 126.8, 130.5, 131.3, 133.7,
135.2, 136.7, 138.8, 143.1, 150.2, 167.1, 173.4. Anal. Calc. for
C21H16O4NBr: C, 59.17; H, 3.78; N, 3.28. Found: C, 59.20; H,
3.75; N, 3.24.
A mixture of kojic acid 1 (1 mmol), aryl aldehyde 2 (1 mmol),
and FAU zeolite nanoparticles (0.008 g) was stirred at 110◦C.
After 10 min, indole 3 (1 mmol) was added and the reaction
was continued for appropriate time. After the completion of the
reaction (as monitored by TLC), water was added with reaction
mixture (15 mL) and extracted with ethyl acetate (3 × 10 mL).
The organic layer was dried over sodium sulfate and concen-
trated under vacuum. The crude product was chromatographed
in silica gel (70:30 n-hexane/ethyl acetate) and appropriate iso-
lated yield is shown in Table 5. The new products were known
2-((1H-Indol-3-yl)(2-nitrophenyl)methyl)-3-hydroxy-6-
1
(hydroxymethyl)-4H-pyran-4-one (4e): H NMR (400 MHz,
DMSO-d6 + CDCl3, 1:4): δ 4.24 (dd, 2H), 5.50 (s, 1H), 6.09
(s, 1H), 6.61 (s, 1H), 7.02–7.21 (m, 3H), 7.37–7.43 (m, 3H),
7.54–7.56 (m, 1H), 7.71–7.74 (m, 1H), 8.09 (d, 1H, J = 8.2),
10.41 (s, 1H). 13C NMR (100 MHz, CDCl3): δ 38.7, 60.1,
1
compounds and characterized by H NMR, 13C NMR spectra
and known compounds were identified by comparing melting
point and 1H NMR spectra with does reported in the literature.
Ph
PhCHO
O
O
2a
O
OH
OH
Catalyst
Solvent, Temprature
+
N
H
HO
N
H
HO
4a
O
3a
SCH. 2. Model reaction for optimization reaction conditions.
1

1500
B. SADEGHI ET AL.
TABLE 1
TABLE 3
Study of BET tests of FAU zeolite nanoparticles
Effect of different solvents on the yield of 4a
Entry
Type of measurement
FAU zeolite Entry
Solvent
Yield (%)
1
2
3
4
5
6
Sample weight (g)
9.11
1
2
3
4
5
6
7
EtOHa
60
20
60
45
10
50
97
Temperature (◦C)
110
THFb
Saturated vapor pressure (KPa)
Mean pore diameter (nm)
89.121
50.239
0.41
DMFa
H2Oa
Total pore volume (cm3.g−1
)
n-Hexanea
Toluenea
Solvent-freeb
As, BET (m2.g−1
)
3.27
a60 min at reflux temperature in 10 mL solvent in the presence of
0.008 g of FAU zeolite nanoparticles.
b60 min at 110◦C in the presence of 0.008 g of FAU zeolite
nanoparticles.
111.1, 119.5, 119.7, 122.2, 123.8, 124.0, 124.4, 127.2, 128.8,
130.9, 132.3, 135.2, 138.8, 141.4, 150.4, 167.8, 176.3. Anal.
Calc. for C21H16O6N2: C, 64.28; H, 4.11; N, 7.14. Found: C,
64.24; H, 4.15; N, 7.16.
1H,), 10.23 (s, 1H). 13C NMR (100 MHz, CDCl3): δ 39.6, 60.2,
111.2, 119.5, 120.3, 122.2, 122.9, 123.9, 124.1, 127.5, 128.8,
130.9, 131.4, 132.2, 134.9, 136.5, 137.4, 145.6, 150.5, 167.6,
176.1. Anal. Calc. for C21H15O6N2Cl: C, 59.09; H, 3.54; N,
6.56. Found: C, 59.12; H, 3.51; N, 6.53.
2-((1H-Indol-3-yl)(3-nitrophenyl)methyl)-3-hydroxy-6-
(hydroxymethyl)-4H-pyran-4-one (4f): H NMR (400 MHz,
1
DMSO-d6 + CDCl3, 1:4): δ 4.22 (dd, 2H), 5.54 (s, 1H), 6.03
(s, 1H), 6.71 (s, 1H), 7.02–7.55 (m, 7H), 8.10 (s, 1H,), 8.23 (s,
1H,), 10.21 (s, 1H). 13C NMR (100 MHz, CDCl3): δ 39.7, 59.7,
111.1, 118.1, 119.5, 120.1, 120.6, 122.2, 122.9, 124.3, 127.5,
129.0 (2C), 131.1 (2C), 136.5, 139.5, 148.3, 151.2, 167.3,
174.2. Anal. Calc. for C21H16O6N2: C, 64.28; H, 4.11; N, 7.14.
Found: C, 64.30; H, 4.09; N, 7.15.
2-((1H-Indol-3-yl)(naphthalene-3-yl)methyl)-3-hydroxy-6-
1
(hydroxymethyl)-4H-pyran-4-one (4i): H NMR (400 MHz,
DMSO-d6 + CDCl3, 1:4): δ 4.20 (dd, 2H), 5.01 (s, 1H), 5.98 (s,
1H), 6.32 (s, 1H), 6.71 (t, J = 7.2 Hz, 1H), 6.85 (t, J = 7.2 Hz,
1H), 7.14–7.67 (m, 9H), 7.85 (s, 1H), 10.19 (s, 1H). 13C NMR
(100 MHz, CDCl3): δ 38.7, 59.4, 108.2, 109.1, 111.5, 118.1,
118.7, 119.4 (2C), 121.5, 123.5, 125.0, 125.9, 126.4, 126.7,
129.6, 130.8, 131.8, 134.1, 134.6, 137.9, 143.5, 152.9, 164.2,
173.3. Anal. Calc. for C25H19O4N: C, 75.55; H, 4.82; N, 3.52.
Found: C, 75.50; H, 4.85; N, 3.56.
2-((1H-Indol-3-yl)(4-nitrophenyl)methyl)-3-hydroxy-6-
1
(hydroxymethyl)-4H-pyran-4-one (4g): H NMR (400 MHz,
DMSO-d6 + CDCl3, 1:4): δ 4.32 (dd, 2H), 5.60 (s, 1H), 6.07 (s,
1H), 6.70 (s, 1H), 7.05 (t, J = 7.4 Hz, 1H), 7,22 (t, J = 7.4 Hz,
1H), 7.35–7.54 (m, 6H), 8.17 (d, 1H, J = 8.3 Hz), 10.15 (s,
1H). 13C NMR (100 MHz, CDCl3): δ 40.2, 59.4, 111.3, 118.1,
119.6 (2C), 122.3 (2C), 123.6 (2C), 126.6, 128.8, 129.5, 130.9,
136.7, 146.5, 151.8, 167.1, 173.5. Anal. Calc. for C21H16O6N2:
C, 64.28; H, 4.11; N, 7.14. Found: C, 64.26; H, 4.13; N, 7.10.
2-((1H-Indol-3-yl)(4-chloro-2-nitrophenyl)methyl)-3-
RESULTS AND DISCUSSION
FAU zeolite nanoparticles were prepared via hydrothermal
method according to experimental section. The synthesized
FAU zeolite nanoparticles were characterized using Fourier
Transform Infrared (FT-IR), X-ray diffraction (XRD), scanning
hydroxy-6-(hydroxymethyl)-4H-pyran-4-one (4h): 1H NMR
(400 MHz, DMSO-d6 + CDCl3, 1:4): δ 4.25 (dd, 2H), 5.75 (s,
1H),6.01 (s, 1H), 6.67 (s, 1H),7.07 (t, J = 7.5 Hz, 1H), 7.23
(t, J = 7.5 Hz, 1H), 7.36–7.55 (m, 5H), 7.86 (s, 1H), 8.05 (s,
TABLE 4
TABLE 2
Effect of catalyst loading on the yield of 4aa
Effect of different catalysts on the yield of 4aa
Entry Amount of catalyst (g) Temperature (◦C) Yield (%)
Entry
Catalyst (g)
Yield (%)
1
2
3
4
5
6
7
8
—
110
110
110
110
100
80
—
50
70
97
85
80
75
97
1
2
3
4
5
6
7
KAl(SO4)2.12H2O (0.01 g)
ZnO-NPs (0.01 g)
60
70
40
40
35
50
97
0.001
0.005
0.008
0.008
0.008
0.008
0.008
CuCl2.2H2O (0.01 g)
SbCl5-SiO2 (0.01 g)
SnCl2.2H2O (0.01 g)
ZnSO4. H2O (0.01 g)
FAU zeolite NPs (0.01 g)
60
120
aReaction conditions: 60 min at 110◦C in solvent-free conditions.
aReaction conditions: 60 min at 110◦C in solvent-free conditions.

SYNTHESIS OF FAU ZEOLITE NANOPARTICLES CATALYST
1501
TABLE 5
Synthesis of 2-substituted aryl (indolyl) kojic acid derivatives by the reaction of kojic acid with aryl aldehyde and indole
derivatives catalyzed by FAU zeolite nanoparticles
Entry
Aldehyde
Indole
Producta
Time (min)
Yield (%)b
M.p (◦C)[Ref]
1
2a
3a
4a
55
97
79–81[9]
2
3
4
5
2b
2c
2d
3a
3a
3a
3a
4b
4c
4d
4e
45
60
60
70
93
87
93
83
93–94[9]
96–98[9]
Oil
2e
87–89
6
2f
3a
4f
85
82
169–171
7
8
2g
3a
3a
4g
4h
75
80
82
85
170–173
167–168
2h
9
2i
3a
3a
4i
4j
85
55
87
92
169–171
79–80
10
2j
11
11
2b
3b
3b
4k
4l
45
50
90
89
84–85[9]
89–90[9]
2c
(Continued on next page)

1502
B. SADEGHI ET AL.
TABLE 5
Synthesis of 2-substituted aryl (indolyl) kojic acid derivatives by the reaction of kojic acid with aryl aldehyde and indole
derivatives catalyzed by FAU zeolite nanoparticles (Continued)
Entry
Aldehyde
Indole
Producta
Time (min)
Yield (%)b
M.p (◦C)[Ref]
12
14
2j
3b
3c
4m
4n
55
70
94
82
86–88[9]
97–98[9]
2c
15
16
2c
2c
3d
4o
4p
65
65
89
93
Oil[9]
Oil[9]
3e
aAll the products were identified by 1H NMR and 13C NMR spectra and also by comparing of melting point and 1H NMR spectra with those
of authentic samples reported in the literature.
bYields refer to isolated products.
electron microscope (SEM), transmission electron microscope run under the same conditions, and similar amounts of catalysts
(TEM), and BET.
(0.01 g) were used. As it is clear in the Table 2, FAU zeo-
The FT-IR spectra of the zeolite is shown in Figure 1. lite nanoparticles resulted in highest conversion to the desired
The spectra shows a broad and strong band at region product.
3200–3600 cm−1. This broad band is due to silanol OH groups
Model reaction was examined in different solvents such as
(Si-OH). The predominant absorbance peak at 979 cm−1 was EtOH, THF, DMF, H2O, n-hexane, and toluene, in the presence
due to Si-O-Al group. The bands between 456 and 740 cm−1 of FAU zeolite nanoparticles (0.008 g) at their reflux temperature
were due to Si-O, Al-O, Si-Al, and Si-O-Si. The absorption (Table 3). The results in Table 3 show the efficiency of solvent-
band at 668 cm−1 was due to Si-O-Na group.
free conditions which gives the desired product in excellent
The dimensions of nanoparticles were observed with XRD yield. This reaction in protic and aprotic solvents did not afford
and SEM. The size of FAU zeolite nanoparticles are about reasonable yield of the product (Table 3, entries 1–6).
50–60 nm. SEM images of FAU zeolite nanoparticles also con-
Increasing the catalyst loading from 0.001 to 0.008 g, in-
firmed that the nanoparticles were homogeneously dispersed in creased the yield of the reaction significantly (Table 4, entries
cubic structure (Figures 2 and 3). It is clearly seen on the TEM 2–4). The best catalyst loading was found in 0.008 g, which
images of FAU zeolite nanoparticles that the crystals size are gave an excellent yield of 4a only after 60 min.
50–60 nm (Figure 4).
The above model reaction was carried out at different temper-
BET results are given in the Table 1. This information in- atures with 0.008 g of FAU zeolite nanoparticles. It was found
cludes the measurement of surface area, total pore volume, and that the desired compound 4a was obtained in excellent yield at
the average pore diameter of FAU zeolite nanoparticles. Ac- 110◦C (Table 4, entries 4–7). Further increase of the temperature
cording to the obtained data, the ideal surface area was obtained (120◦C) neither increased the yield nor shortened the reaction
approximately 3.27 m2/g and the average pore diameter was time (Table 4, entry 8).
obtained 50.2 nm.
A series of aromatic aldehydes 2 were treated with kojic
To obtain optimal conditions, the reaction between benzalde- acid 1 and indole derivatives 3 in the presence of FAU zeolite
hyde with indole and kojic acid was regarded as model reaction nanoparticles (0.008 g) under solvent-free conditions at 110◦C
(Scheme 2).
(Table 5). Benzaldehyde and 2-naphthaldehyde were treated
To emphasize the effect of the catalyst, a series of different with kojic acid and indole, and the corresponding 2-substituted
catalysts were applied for the model reaction. All reactions were aryl (indolyl) kojic acid derivatives were produced in excellent

SYNTHESIS OF FAU ZEOLITE NANOPARTICLES CATALYST
1503
yields (Table 5, entries 1 and 10). When kojic acid and indole catalyst, which make it a useful, attractive, and green strategy
reacted with aldehydes such as 3-phenoxy, 4-methoxy, and 4- for formation of a wide range of 2-substituted aryl (indolyl)
methyl benzaldehyde, the corresponding product was formed kojic acid derivatives.
with 87 to 93% yields (Table 5, entries 2–4). Aromatic alde-
hyds including halogen group and electron-withdrawing group
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in good yields (Table 5, entries 5–9).
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2. Xiong, W.N.; Yang, C.G.; Jiang, B. Bioorg. Med. Chem. 2001, 9, 1773.
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Interestingly, substituted indoles were also effective for this
three-component reaction. When 2-methyl indole were reacted
with kojic acid and aldehydes such as 3-phenoxy, 4-methoxy
benzaldehyde, and 2-naphthaldehyde under the same reaction
conditions, a higher yield of the 2-substituted aryl (indolyl) ko-
jic acid product was obtained in shorter times (Table 5, entries
11–13). Similarly, when 2-phenyl, 5-chloro, and 5-bromo in-
dole reacted with 4-methoxy benzaldehyde and kojic acid in
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good yield of the corresponding products was obtained (Table 5,
entries 14–16).
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CONCLUSION
In summary, we have reported an efficient procedure for one-
pot synthesis of 2-substituted aryl (indolyl) kojic acid derivatives
through three-component reactions of kojic acid with indoles
and aryl aldehydes using a catalytic amount of FAU zeolite
nanoparticles under solvent-free conditions. By incorporating
two biologically potential moiety in a single molecule, the bi-
ological activity of these compounds may be enhanced. The
main advantages of this procedure include high yields, sim-
ple experimental procedure, short-reaction times, use of various
substrates, ease of the work-up, nonuse of hazardous organic sol-
vents, and use of heterogeneous and environmentally friendly
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