Efficientone-pot synthesis of imidazoles catalyzed by silica-supported La0.5Pb0.5MnO3 nano particles as anovel and reusable perovskite oxide

Article abstract of DOI:10.4314/bcse.v32i1.15

Silica-supported La0.5Pb0.5MnO3 nanoparticles was prepared and used as a new perovskite-type catalyst for rapid and efficient synthesis of substituted imidazoles by an one-pot three-component condensation of [9,10]-phenanthraquinone, aryl aldehydes and ammonium acetate in excellent yield under reflux, and also solvent-free conditions.

Full text of DOI:10.4314/bcse.v32i1.15

Bull. Chem. Soc. Ethiop. 2018, 32(1), 157-166.
 2018 Chemical Society of Ethiopia and The Authors
DOI: https://dx.doi.org/10.4314/bcse.v32i1.15
ISSN 1011-3924
Printed in Ethiopia
EFFICIENTONE-POT SYNTHESIS OF IMIDAZOLES CATALYZED BY SILICA-
SUPPORTED La0.5Pb0.5MnO3 NANO PARTICLES AS ANOVEL AND REUSABLE
PEROVSKITE OXIDE
Najmeh Zahedi1,2, Ali Javid2*, Mohammad Kazem Mohammadi2 and Haman Tavakkoli2
1Department of Chemistry, Khouzestan Science and Research Branch, Islamic Azad University,
Ahvaz, Iran
2Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
(Received December 09, 2017; Revised February 11, 2018; Accepted February 15, 2018)
ABSTRACT. Silica-supported La0.5Pb0.5MnO3 nanoparticles was prepared and used as a new perovskite-type
catalyst for rapid and efficient synthesis of substituted imidazoles by an one-pot three-component condensation of
[9,10]-phenanthraquinone, aryl aldehydes and ammonium acetate in excellent yield under reflux, and also solvent-
free conditions.
KEY WORDS: Perovskite, Multicomponent reaction, One-pot synthesis,Imidazoles, Nano catalyst,
Heterogeneous catalyst
INTRODUCTION
Imidazole derivatives are an important group of heterocyclic compounds that have biological
and chemical properties [1]. Nowadays these compounds are used in pharmacology. They have
different capacity such as anti-bacterial, anti-viral, and anti-cancer, anti-inflammatory [2-4].
Also, the imidazole ring system is one of the main substructures found in most of natural
products and pharmacologically active compounds, such as the hypnotic agent [5]. Therefore, a
great number of synthetic methods have been reported for the synthesis of multi substituted
imidazoles [6].
In the last decade, 2,4,5-trisubstituted imidazoles are synthesized by one-pot three-
component compression of an aldehyde and ammonium acetate with an α-hydroxy ketone, or an
α-keto-oxime, or a 1,2-dicarbonyl compound by using various catalyst such as ionic liquids
[7,8], Lewis acids [9,10], protic acids [11-13], and other catalysts [14-17]. However, most of
these methodologies are associated with one or more disadvantages, such as low yields, high
temperature requirement, longer reaction time, highly acidic conditions, use of expensive
reagents and catalysts, requirement of large amount of catalysts, use of harmful solvents,
formation of toxic wastes and tedious work-up [8].
Perovskite-type oxides with the chemical formula ABO3 can be crystallized with cubic
structure. The level of oxygen and defects is affected by the composition because of a wide
constancy range of the structure. The greater A-site cation mostly represents a metal cation
belonging to one of groups of rare earth metals (La, Sm, Pr), alkaline earth metals (Sr, Ba, Ca),
or alkali metals (Na, K) coordinated to 12 oxygen anions. The B-site cation represents typical
normally a smaller transition metal cation, which occupying occupies octahedral spaces in the
oxygen framework. Some hybrids of A- and B-site cations can create a steady perovskite-like
structure [18]. The catalytic activity of perovskite-type catalysts is mainly because of the
existence of the multiplicity of oxidation states [19]. Perovskite-type oxides possess adsorption,
acid-base, as well as redox properties, which leads to attractive catalytic activities. They can
fulfil the requirements (excellent activity, constancy, and potential to be processed into
structured catalysts) [20].
__________
*Corresponding author. E-mail: alijavids@yahoo.com
This work is licensed under the Creative Commons Attribution 4.0 International License

158
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Herein, in continuation of our interest to perovskite-type oxides [21, 22], and our works with
solid acids as heterogeneous catalyst in organic reactions [23-28], in this study we wish to report
the synthesis of imidazole derivatives (3a–j) via a one-pot three-component condensation of
9,10-phenanthraquinone (1), aromatic aldehyde (2a-j), and ammonium acetate in the existence
of perovskite-type oxide La0.5Pb0.5MnO3(LPMO) nanoparticles and La0.5Pb0.5MnO3 supported on
silica (S-LPMO) as a new catalyst, in reflux and solvent-free conditions (Scheme 1).
Scheme 1. One-pot three component synthesis of substituted imidazolesin the presence of
perovskite catalyst.
EXPERIMENTAL
General
All materials and reagents were purchased from Merck and Aldrich and utilized with no more
purification. Determination of melting points were carried out using an Electro thermal type
9100 melting point apparatus and are uncorrected. The IR spectra were recorded on a Thermo
Nicolet AVATAR-370 FT-IR spectrophotometer. A Bruker DRX250 spectrometer was used to
obtain 1H NMR spectra.
Preparation of La0.5Pb0.5MnO3 nano particles
In current study, the perovskite precursor was synthesized using the citrate-based sol-gel
improved Pechini technique [21]. Chemicals of La(NO3)3.6H2O, C6H9MnO6.2H2O, Pb(NO3)2
and citric acid (99.5%) were utilized as raw materials. Next, a mixture of metal nitrates solutions
with nominal La:Pb:Mn ratios of 0.5:0.5:1 (LPMO) was prepared in deionized water. The
addition of citric acid to the metal solution was performed proportionally to have the similar
o
equivalents. The solution was concentrated through evaporation at nearly 50 C with agitating
for 1 h for converting them to steady (La, Pb)/CA complexes. The solution was agitated on a hot
o
plate at about 75 C for removing excess water and accelerating polyesterification reaction.
o
Next, the dry gel was achieved thought heating gradually to 120 C in an oven. The gel pieces
were milled to create a fine powder. Finally, La0.5Pb0.5MnO3 NPs were synthesized through
thermal treating the precursor at 650 oC for 9 h in air. Most of the residual carbon was removed
trough annealing of the amorphous precursor and the hexagonal perovskite phase was achieved.
Preparation of silica-supported La0.5Pb0.5MnO3 nanoparticles (30% w/w)
o
Initially silica was put into oven for 2 hours with 90 C, then catalyst (0.3 g) with silica (0.7 g)
were worn out into glass mortar about 1 hour when mixture were bright and unify.
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Synthesis of imidazoles catalyzed by silica-supported La0.5Pb0.5MnO3 nano particles
159
Typical procedure synthesizing imidazole derivatives in reflux condition
A mixture of aldehyde (1 mmol), 9,10-phenanthraquinone (1 mmol), ammonium acetate (2.5
mmol) and S-LPMO nanoperovskite (0.04 g) in 10 mL ethanol was stirred. The resulted mixture
was refluxed for described time. At the end of the reaction (the reaction progress was monitored
by TLC using n-hexan:ethylacetateas eluent solution) the catalyst was separation with filtering,
and solid perovskite catalyst was isolated and could be reused. The solid product resulted after
evaporation of organic phase, was washed with cold water (3 × 20 mL), and recrystallized in
ethanol to provide pure product.
Typical process for synthesizing imidazole derivatives in solvent-free condition
A mixture of aldehyde (1 mmol), 9,10-phenanthraquinone (1 mmol), ammonium acetate (2.5
mmol) and S-LPMO nano perovskite (0.04 g) was stirred. Then, the mixture was heated at a
temperature of 100 oC for described time (the reaction progress was monitored by TLC using n-
hexan:ethylacetate as eluent). After cooling, the filtration of mixture was carried out and the
filtrated mixture was washed using ethanol to separated catalyst. The filtrate was concentrated
through evaporation under reduced pressure using a rotary evaporator. To obtain pure products,
the recrystallization of remaining solid from ethanol was carried out.
Analytical data for selected compounds
2-(4-Nitrophenyl)-1H-phenanthro[9,10-d]imidazole (3b). Yellow crystal, m.p. = 316 oC. IR
(KBr):  = 3260 (N-H), 1591 (C=N), 1536 (NO2), 1450 (C=C), 1383 (NO2) cm-1. 1H NMR (250
MHz, DMSO-d6): δ = 7.63-8.83 (m, 12 H, Ar-H), 13.80 (s, 1H, NH) ppm.
o
2-(2-Chlorophenyl)-1H-phenanthro[9,10-d]imidazole (3e). Yellow crystal, m.p. = 232-234 C.
IR (KBr):  = 3435 (N-H), 1594 (C=N), 1450 (C=C) cm-1. 1H NMR (250 MHz, DMSO-d6): δ =
7.37-8.88 (m, 12H, Ar-H), 13.57 (s, 1H, NH) ppm.
2-(p-Tolyl)-1H-phenanthro[9,10-d]imidazole (3h). Yellow crystal, m.p. = 290-292 oC. IR
1
(KBr):  = 3377 (N-H), 1612 (C=N), 1593 (C=C) cm-1. H NMR (250 MHz, DMSO-d6): δ =
2.38 (s, 3H, CH3), 7.28-8.82 (m, 12 H, Ar-H), 13.36 (s, 1H, NH) ppm.
2-(4-(Benzyloxy)phenyl)-1H-phenanthro[9,10-d]imidazole (3i). Yellow crystal, m.p. = 228-230
oC. IR (KBr):  = 3432 (N-H), 1592 (C=N), 1673 (C=C) cm-1. 1H NMR (250 MHz, DMSO-d6):
δ = 5.11 (s, 2H, CH2), 7.16-8.83 (m, 17 H, Ar-H), 9.83 (s, 1H, NH) ppm.
N-(4-(1H-Phenanthro[9,10-d]imidazol-2-yl)phenyl)acetamide (3j). Yellow crystal, m.p. = 246-
248 oC. IR (KBr):  = 3212 (N-H), 1591 (C=N), 1562 (C=C) cm-1. 1HNMR (250 MHz, DMSO-
d6): δ = 2.08 (s, 3H, CH3), 7.28-8.82 (m, 12H, Ar-H), 10.17 (s, 1H, NH), 13.40 (s, 1H, NH)
ppm.
RESULTS AND DISCUSSION
After synthesis of La0.5Pb0.5MnO3 nanoparticles [21], for characterization of this catalyst, the
morphology of the sample was determined using SEM analysis. Figure 1 demonstrates the
micrograph related to the samples prepared through the sol-gel modified Pechini technique and
calcined 650 oC.
According to the SEM images, the surface is obviously porous and it appears that the size of
grown particles is uniform. The size of pores is in the range of 30-188 nm. Moreover, SEM
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Najmeh Zahedi et al.
image shows that besides the
ppresence of bigger particles, there were relatively smaller paarticles
on the surface. However, the main particles on the surface were the bigger oness. The
aggregation of smaller particl
on the surface.
ees (in the nm scale) may cause the creation of larger LPMO NPs
Figure 1. SEM image of La0.5PPb0.5MnO3 nanoparticles.
Figure 2. FTIR spectrum of La0.5Pb0.5MnO3 nanoparticles.
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Synthesis of imidazoless catalyzed by silica-supported La0.5Pb0.5MnO3 nano particles
161
Figure 3. FTIR spectrum of si
l
ica-supported La0.5Pb0.5MnO3 nanoparticles.
FT-IR spectra were obtai
n
ed for single LPMO and S-LPMO samples in range of 40
0
-4000
cm-1. Figure 2 shows the FT-I
RR spectrum of LPMO perovskite nanoparticle, and Figure 3 shows
the FT-IR spectrum of S-LPMO sample. The IR bands at 3430 and 1638 cm-1 is due to the
stretching and bending vibratioon of H2O molecules, respectively. The very strong and IR band at
1113 cm-1 is usually assigned to the Si-O-Si asymmetric vibrations. The picks at 668 a
n
n
d 592
cm-1 corresponding to LPMO perovskite coated on SiO2 are clearly observed in this sp
[18, 21].
eectrum
For the purpose of optimi
were executed various amou
out on the synthesis of 2-(4-chlorophenyl)-1H-phenanthro[9,10-d]imidazole (3
condensing [9,10] phenanthra uinone (1 mmol), 4-choloro benzaldehyde (1 mmol), ammonium
acetate (2.5 mmol) in ethanol. For establish effectiveness of LPMO, a test reaction done ithout
catalyst at ambient temperatu e. We were performed trace amount of product in the absence of
catalyst (entry 1). We increa ed temperature up to reflux condition, but final product wwas not
z
nn
ation of the amount of catalyst and the reaction time, initially we
t catalyst in presence ethanol solvent. A model study was carried
via
gg)
qq
ww
r
r
s
s
appreciable (entry 2). After that, reactions were reacted with different amounts of LPMO
catalyst. Results summarized in Table 1 indicated the best result was with 0.04 g amount of
catalyst but increasing the a
mmount of catalyst did not improve the yield (entry 6 and 7).. Also,
when we supported LPMO on silica (S-LPMO), the amount of product was increased (entrry 8).
Table 1. Effect of catalyst on the oo
ne-pot three component synthesis of substituted imidazolea
Entry
Catalyst/g
Temperature (oC)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
0.0
0.0
R.T.
12
12
2
2
2
2
2
2
Trace
<25
40
53
62
74
73
94
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
LPMO/0.01
LPMO/0.02
LPMO/0.03
LPMO/0.04
LPMO/0.05
S-LPMO/0.04
aReaction conditions: 4-choloro be
(2.5 mmol) in ethanol.
nnzaldehyde (1 mmol), [9,10]phenanthraquinone (1 mmol), ammonium acetate
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Considering solvent plays a key role in reactions, reaction was reacted in presence different
solvents. Results are presented in Table 2. We observed protic solvent including ethanol and
methanol have higher yield in this method. The best result was achieved using ethanol(entry 3).
This reaction had proper result in free solvent condition. Thus this reaction was considered in
free solvent reaction similarly.
Table 2. Effect of solvent on the one-pot three component synthesis of substituted imidazolea
Entry
solvent
CHCl3
MeOH
EtOH
Yield (%)
1
2
3
64
78
94
4
5
DMF
42
80
Solvent free (100°C)
a. Reaction conditions: 4-choloro benzaldehyde (1mmol), [9,10]phenanthraquinone(1mmol), ammonium acetate
(2.5 mmol) and S-LPMO catalyst (0.04 gr) at reflux condition after 2 hours.
At the end of the model reaction, the nano catalyst was separated from the reaction mixture,
washed with acetone and dried at 100°C under vacuum for 2 h and reapplied four times for the
same reaction. As presented in Table 3, the catalyst can be reused at least four times with no
change in its activity.
Table 3. Effect of catalyst recycling on the one-potthree component synthesisof substituted imidazolea
Runs
Yield (%)
1
2
94
93
3
4
93
90
a. Reaction conditions: 4-choloro benzaldehyde (1mmol), [9,10]phenanthraquinone (1mmol), ammonium acetate
(2.5 mmol) and S-LPMO catalyst (0.04 gr) at reflux condition in ethanol after 2 hours.
Table 4. One-pot three component synthesis of substituted imidazoles using La0.5Pb0.5MnO3 nanoparticles
supported on silicaas an acidic catalysta
Entry Ar
Product Yield (%)
reflux/solvent-
m.p. (oC)
found/reported [Ref.]
free
1
2
C6H5
4-NO2C6H4
3a
3b
89 / 78
92 / 77
286-288/>300 [17]
>300/>300 [17]
3
3-NO2C6H4
3c
89 / 75
269-271/278-280 [13]
4
5
6
7
4-CNC6H4
2-ClC6H4
4-ClC6H4
3d
3e
3f
86 / 71
87 / 79
94 / 80
83 / 76
>300/>300 [17]
232-234/236-237 [17]
268-270/263-265 [13]
258-260/265-267 [13]
4-MeOC6H4
3g
8
9
10
4-MeC6H4
4- PhCH2OC6H4
4-H3CONHC6H4
3h
3i
3j
84 / 82
68 / 60
74 / 66
290-292/292-294 [13]
228-230/ new
246-248/ new
aReaction conditions: aldehyde (1 mmol), [9,10]phenanthraquinone (1 mmol), ammonium acetate (2.5 mmol) and
S-LPMO catalyst (0.04 g), at reflux condition in ethanol after 2 hours.
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Synthesis of imidazoles catalyzed by silica-supported La0.5Pb0.5MnO3 nano particles
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Scheme 2. Plausible mechanism for the formation of imidazole derivatives in the presence of S-
LPMO catalyst.
Finally, after optimizing the reaction conditions, we prepared a range of replaced imidazoles
(Table 4). In all cases, aldehydes reacted effectively with replaced carrying either electron-
donating (entries 7-10) or electron-withdrawing (entry 2-4) groups and provided the estimated
products in good to yields.
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The mechanism of the reaction was proposed in Scheme 2. Ammonia molecules are
obtained from ammonium acetate. We think that the aldehyde and 1,2-dicarbonyl compounds
including 9,10-phenanthraquinone at first activated by S-LPMO as Lewis acid, in the rate
determining step.
CONCLUSION
In conclusion, we benefit from one pot synthesis for the preparation of substituted imidazoles
through three-component condensation of aldehyde, 9,10-phenanthroquinone, and ammonium
acetate in presence of silica-supported La0.5Pb0.5MnO3 nanoparticles as an efficient, re-usable
and green solid acid catalyst, in reflux and solvent-free conditions. This catalyst has enhanced
specific surface area, therefore increasing the contact between the catalyst and reactant.
Excellent yields, short reaction times, simplicity of operation and easy separation and re-
usability of catalyst are several advantages of this technique. Recovery of both products and
inorganic support/catalyst is generally possible, leading to an effective and low-waste route to a
range of products.
ACKNOWLEDGEMENT
The authors are grateful to Islamic Azad University, Ahvaz Branch for financial support.
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