A facile one-pot synthesis of tetrasubstituted imidazoles catalyzed by eutectic mixture stabilized ferrofluid

Article abstract of DOI:10.1016/j.molliq.2014.03.013

A robust and simple one-pot four component reaction for the efficient synthesis of tetrasubstituted imidazoles has been developed. In the presence of eutectic mixture stabilized iron oxide nanoparticles, the four-component reaction of aldehydes, amines, ammonium acetate, and 1,2-diphenylethane-1,2- dione proceeds smoothly at 60 °C to give a range of imidazole derivatives in moderate to good yields. Target compounds were obtained in high yields and high purity after recrystallization from ethanol.

Full text of DOI:10.1016/j.molliq.2014.03.013

MOLLIQ-04189; No of Pages 6
Journal of Molecular Liquids xxx (2014) xxx–xxx
Contents lists available at ScienceDirect
Journal of Molecular Liquids
journal homepage: www.elsevier.com/locate/molliq
1
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A facile one-pot synthesis of tetrasubstituted imidazoles catalyzed by
eutectic mixture stabilized ferrofluid
Q23Q1 Najmoddin Aziizi, Zohreh Manochehri, Adnan Nahayi, Sohila Torkashvand
4
Department of Biology and Environment, Islamic Azad University, Parand Branch, Tehran, Iran
5
a r t i c l e i n f o
a b s t r a c t
OOF
6
7
8
9
10
Article history:
A robust and simple one-pot four component reaction for the efficient synthesis of tetrasubstituted imidazoles 17
has been developed. In the presence of eutectic mixture stabilized iron oxide nanoparticles, the four-component 18
reaction of aldehydes, amines, ammonium acetate, and 1,2-diphenylethane-1,2-dione proceeds smoothly at 19
60 °C to give a range of imidazole derivatives in moderate to good yields. Target compounds were obtained in 20
Received 10 February 2014
Received in revised form 8 March 2014
Accepted 12 March 2014
Available online xxxx
high yields and high purity after recrystallization from ethanol.
21
22
11
© 2014 Elsevier B.V. All rights reserved.
Keywords:
12
13
14
15
16
Aldehyde
Ferrofluid
1,2-Diphenylethane-1,2-dione
Imidazole
Amine
26
34
25
2Q7 3 1. Introduction
an aldehyde and amine (modified Debus reaction) was an efficient 53
and economical synthetic route to be well-designed highly substituted 54
imidazole derivatives. In this context, a great variety of catalyst, pro- 55
moter and solvent have been developed for the synthesis of 1,2,4,5- 56
tetrasubstituted imidazoles reported in the literature [21–47]. Most of 57
these procedures suffer from one or more serious drawbacks, such as 58
expensive and hazardous acid catalysts, occurrence of side reactions, 59
low yields and the use of expensive and excess reagents. Therefore, 60
the development of a new and efficient catalytic system to overcome 61
these shortcomings and use mild, efficient and environmentally benign 62
protocol for the synthesis of highly substituted imidazoles is an impor- 63
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
Naturally occurring heterocycles such as substituted imidazoles, as
well as synthetic derivatives thereof, play an important role in chemical
and biological systems [1,2]. Many of the substituted imidazoles are
known as plant growth regulators and attractive targets in medicinal
chemistry as the antiulcerative agent cimetidine, the proton pump
inhibitor omeprazole, the fungicide ketoconazole, the benzodiazepine
antagonist flumazenil and anticancer agents [3].
In green chemistry imidazole derivatives used as ionic liquids can
be used as electrolytes or green solvents because of their low vapor
pressure and wide chemical stability [4]. Furthermore, imidazolylidene
based carbenes have been investigated as efficient ligands in coordina-
tion chemistry, as powerful steering/controlling elements in organome-
tallic catalysis [5], and metal-free catalysts for organic reactions [6,7]. In
addition, fluorescence and chemiluminescence properties of imidazole
scaffolds have received great attention in material chemistry for the
development of fluorescence labeling agents and blue light emitting
materials [8–11].
tant task in the planning of organic synthesis.
64
2. Results and discussion
65
As part of our interest in the development of efficient protocols 66
for the synthesis of simple starting material herein, we report the exten- 67
sion of this methodology to the synthesis of novel tetrasubstituted 68
imidazoles under mild reaction conditions. Intensive experimentation 69
with different reactions under various conditions was carried out to 70
find the optimal reaction conditions. In the model reaction of 3enzyl 71
(1 equiv.), benzaldehyde (1 equiv.), aniline (1 equiv.) and ammonium 72
acetate (1 equiv.) in eutectic mixture stabilized ferrofluids, a safe cata- 73
lyst and reaction media were studied. The use of ferrofluids, in eutectic 74
mixture at room temperature was unsuccessful and imine products and 75
the 3enzyl were recovered. Increasing the temperature to 60 °C, 90% 76
yield of the desired product were obtained (Scheme 2). Next, in the 7Q76
search for optimal reaction conditions, solvent-less condition and a 78
wide variety of solvents were explored and results are summarized in 79
Owing to the wide applicability of imidazoles in the industry and
laboratory, there areUa numNber Cof divOergentRmethRods toEpreCpare TED PR
4Q7 4 substituted imidazoles in the literature. Among the several approaches
48
49
50
51
that are available for synthesis of imidazoles, Debus, Wallach, Van
Leusen, Marckwald and Radiszewski methods [12–20] received great
attention, and increasing interest has been devoted to find the catalyst
and promoter to reach the high yields of pure products (Scheme 1).
5Q2 5 One-pot multi-component cyclocondensation of a 1, 2-diketone, with
E-mail address: payam5245@yahoo.com (Z. Manochehri).
http://dx.doi.org/10.1016/j.molliq.2014.03.013
0167-7322/© 2014 Elsevier B.V. All rights reserved.
Please cite this article as: N. Aziizi, et al., Journal of Molecular Liquids (2014), http://dx.doi.org/10.1016/j.molliq.2014.03.013

2
N. Aziizi et al. / Journal of Molecular Liquids xxx (2014) xxx–xxx
O
O
NHCH2R
NHCH2R
PCl5
+
HI
R
R
O
O
R
R
R
R
O
RNH2
+
+
O
N
R
(H or R)
KSCN
+
R
N
NH2
H
O
RNH2
+
+
Tos
N
R
H
Scheme 1. Imidazole prepration in the litrature.
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
Scheme 1. Changing the solvent from DES to ethanol was not beneficial
as the yield was reduced to 70%. Other solvents, such as acetonitrile,
tetrahydrofuran, and toluene were ineffective for this transformation.
Furthermore, in the absence of ferrofluids, 25% yield of the desired prod-
uct was obtained.
With a suitable reaction system in hand, to delineate this approach,
particularly in regard to library construction, this methodology was
evaluated by using different aldehydes, 1,2-diketones, and amines.
Three commercially available 1,2-diketones 1, aromatic amines 2, and
commercially available aldehydes 3, were chosen for the library valida-
tion, and selected examples were shown in Table 1.
At the beginning of the search for the scope of the aldehyde
substrate, ammonium acetate, 4enzyl and aniline were used as model
substrates and the results indicated that all commercially available
aldehydes were good substrate for this system (Table 1). Aromatic
aldehydes bearing such functional groups as chloro, bromo, methyl, or
methoxy were able to affect the imidazole synthesis. We have also
observed that the electronic effect on the aldehydes had little influence
on the yield and time of reaction conditions: that is, aryl aldehydes
with electron-withdrawing groups reacted rapidly, while substitution
Further research is needed to postulate the exact reaction mecha- 112
nism, the proposed mechanism proceeds via ring contraction of activat- 113
ed aldehyde and benzil via hydrogen bonding in DES. DES plays a triple 114
role in this reaction; as ionic reaction media, as hydrogen bond catalysis 115
and stabilization of Fe3O4 nanoparticle. However, the same reaction in 1Q176
the absence of Fe3O4 in DES gives low yields of products and indicated 117
the essential role of this magnetic nanoparticle. The results indicated 118
that the physical and chemical properties of the Fe3O4 in DES especially 119
their Lewis acid sites had a significant influence on the catalytic activity. 120
3. Conclusions
121
In conclusion, we have demonstrated an efficient and simple meth- 122
od for the preparation of tetrasubstituted imidazole derivatives using 123
readily available starting materials. Prominent among the advantages 124
of this new method are operational simplicity and good yields. The 125
separation and purification process are very simple and convenient, 126
only needing recrystallization. Starting materials are inexpensive and 127
commercially available.
128
100 of electron-rich groups on the benzene ring did not decrease the
101 reactivity. In addition, the 2-furaldehyde, 2-naphthaldehyde and 1-
102 naphthaldehyde also gave good yields of products.
4. Experimental section
129
1H NMR spectra were recorded on a 500 MHz spectrometer and 13
C
130
103
Encouraged by this success, some aromatic amines, and 1,2-
104 diketones were also used as substrates. The electronic effect of the
105 substituted in arylamines and 1,2-diketones showed a remarkable influ-
106 ence on the reaction; electron-rich arylamines such as 4-methylaniline
107 and 4-methoxyaniline gave well to excellent yields, but moderate yields
108 were obtained from the reactions of electron-deficient arylamines such
109 as 4-chloroaniline and 4-bromoaniline. However, highly electron-
110 deficient amines such as 4-nitroaniline and 2-nitroaniline resulted in
111 no reaction under optimized reaction condition (Table 2).
NMR spectra were recorded on a 125 MHz NMR spectrometer using 131
CDCl3 or DMSO(D6), as a solvent; chemical shifts have been expressed 132
in ppm downfield from TMS. IR spectra were recorded on a Perkin- 133
Elmer 683 or 1310 FT-IR spectrometer in KBr pellets. M. P. were record- 134
ed on Buchi 535 melting point apparatus and are uncorrected. All 135
starting materials are commercially available and were purchased and 136
used without further purification. Water and other solvents were 137
distilled before used.
138
NH2
CHO
Ph
Ph
Ph
Ph
O
O
N
Fe3O4
Ph
+
NH4OAc
+
+
N
Solvent, (1 mL)
60oC, 2 h
Ph
3
1
4
2
Solvent
Yields (%)
Toluene MeCN THF Neat Water, EtOH
40 70 45 40 50 70
DES
90(25)a
a without catalyst DES: urea-choline chloride
Scheme 2. Optimization of reaction conditions.
Please cite this article as: N. Aziizi, et al., Journal of Molecular Liquids (2014), http://dx.doi.org/10.1016/j.molliq.2014.03.013

N. Aziizi et al. / Journal of Molecular Liquids xxx (2014) xxx–xxx
3
t1:1
t1:2
Table 1
Synthesis of 1,2,4,5-tetrasubstituted imidazoles under mild reaction condition.
OOF
t1:3
aNMR yields.
139 5. Preparation of a eutectic mixture ferrofluid [50]
electron Microscopy (SEM) and Fourier transform infrared spectros- 152
copy (FT-IR) (Figs. 1–3).
153
UNCORRECTED PR
140
In a typical procedure, FeSO4.7H2O, (10 g) were dissolved in
141 30 mL of deionized water and 30 mL of urea-choline chloride base
142 eutectic mixture under nitrogen atmosphere and reaction mixture
143 were heated. At 90 °C a solution of 0.8 g KNO3 and 6 g KOH in 6 mL
144 H2O was added dropwise for 5 min to the Fe (II) solution, under ni-
145 trogen bubbling. After 60 min of stirring, the black precipitate was
146 formed. The black powder obtained was stirred over 2 h at 90 °C,
147 left overnight and then washed with water and ethanol and separat-
148 ed magnetically. The Fe3O4 nanoparticles (0.05 g) were suspended in
149 deep eutectic solvent (1 mL) by ultrasound irradiation. The crystal
150 phase, purity, particle size and morphology of the Fe3O4 nanoparti-
151 cles were determined by powder X-Ray diffraction (XRD), Scanning
5.1. General procedure
154
A mixture of benzil (1 mmol), aldehyde (1 mmol) primary amine 155
(1 mmol), ammonium acetate (1 mmol) and eutectic mixture stabi- 156
lized ferrofluids (0.05 g of Fe3O4 in 1 mL of urea-choline chloride 157
based eutectic mixture) was heated at 60 °C with stirring for 2–6 h. 158
After completion of the reaction, the mixture was cooled to room tem- 159
perature and water was added and products recrystallized in ethanol. 160
All compounds were characterized on the basis of their spectroscopic 161
data (IR, NMR) and by comparison with those reported in the literature. 162
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N. Aziizi et al. / Journal of Molecular Liquids xxx (2014) xxx–xxx
t2:1
t2:2
Table 2
Synthesis of tetrasubstituted imidazoles.
t2:3
aNMR yields.
250
200
150
100
50
0
20
30
40
50
60
70
80
Fig. 1. X-ray diffraction pattern of Fe3O4 nanoparticles.
Fig. 2. FT-IR spectra of (Fe3O4) nanoparticles.
Please cite this article as: N. Aziizi, et al., Journal of Molecular Liquids (2014), http://dx.doi.org/10.1016/j.molliq.2014.03.013

N. Aziizi et al. / Journal of Molecular Liquids xxx (2014) xxx–xxx
5
Fig. 3. Scanning electron microscopy (SEM) images of (Fe3O4) nanoparticles.
163 5.2. Selected data
5.2.8. (Table 1, 4l) 2-(2,4-dichlorophenyl)-1,4,5-triphenyl-1H-imidazole
206
1H NMR, 500 MHz (DMSO-d6) δ 7.12–7.31 (m, 13H), 7.42 (dd, J = 7.9, 207
1.5 Hz, 1H), 7.50 (d, J = 7.5 Hz, 2H), 7.60–7.62 (m, 2H): 13C NMR 208
(125 MHz, DMSO-d6) δ 127.2, 127.4, 127.9, 128.9, 129.0, 129.3, 129.4, 209
129.5, 129.7, 130.2, 130.9, 131.5, 135.7, 136.3, 137.7, 144.2, MS (m/z, %): 210
OOF
164 5.2.1. (Table 1, 4b) 2-(4-Chlorophenyl)-1,4,5-triphenyl-1H-imidazole
165
1H NMR, 500 MHz (CDCl3) δ 7.08 (d, J = 6.9 Hz, 2H), 7.15 (d, J =
166 6.9 Hz, 2H), 7.26–7.33 (m, 11H), 7.42 (d, J = 7.8 Hz, 2H), 7.63 (d, J =
167 8.7 Hz, 2H): 13C NMR (125 MHz, CDCl3/DMSO-d6) δ 127.4, 127.9,
168 128.6, 128.7, 128.8, 129.1, 129.7, 130.4, 130.7, 131.5, 136.9, 145.9: MS
169 (m/z, %): 406 (M+), 165 (100).
441 (M+), 165 (100).
211
5.2.9. (Table 1, 4s) 2-(naphthalene-3-yl)-1,4,5-triphenyl-1H-imidazole
212
1H NMR, 500 MHz (CDCl3) δ 7.12 (d, J = 7.12 Hz, 2H), 7.19 (d, J = 213
7.4 Hz, 2H), 7.24–7.35 (m, 9H), 7.45–7.50 (m, 2H), 7.56 (d, J = 8.4 Hz, 214
1H), 7.68–7.72 (m, 4 H), 7.79 (d, J = 7.8 Hz, 1H), 8.00 (s, 1H): 13C 215
NMR (125 MHz, CDCl3) δ 126.6, 126.7, 127.0, 127.3, 128.0, 128.1, 216
128.5, 128.6, 131.5, 131.6, 133.3, 133.4, 137.3, 147.1: MS (m/z, %): 422 217
170 5.2.2. (Table 1, 4c) 2-(4-bromophenyl)-1,4,5-triphenyl-1H-imidazole
171
1H NMR, 500 MHz (DMSO-d6) δ 7.16–7.33 (m, 15H), 7.48 (d, J =
172 7.08 Hz, 4H): 13C NMR (125 MHz, CDCl3/DMSO-d6) δ 122.7, 127.2,
173 127.4, 129.0, 129.3, 129.5, 129.7, 130.4, 131.0, 131.9, 132.0, 132.4,
174 135.1, 137.2, 137.9, 145.8; MS (m/z, %): 450 (M+, 100).
(M+, 100).
218
175 5.2.3. (Table 1, 4d) 4-(1,4,5-triphenyl-1H-imidazole-2-yl)phenol
176
5.2.10. (Table 1, 4r) 2-(naphthalene-1-yl)-1,4,5-triphenyl-1H-imidazole 219
1H NMR, 500 MHz (CDCl3) δ 6.93 (d, J = 7.0 Hz, 2H), 7.00–7.09 (m, 220
3 H), 7.26–7.52 (m, 12 H), 7.72 (dd, J = 7.2, 1.2 Hz, 2H), 7.83 (t, J = 221
7.4 Hz, 2 H), 8.24 (dd, J = 6.8, 2.2 Hz, 1H): 13C NMR (125 MHz, CDCl3) 222
δ 125.0, 126.4, 126.6, 127.1, 127.9, 128.2, 128.3, 128.4, 128.5, 128.6, 223
128.9, 129.0, 129.8, 129.9, 130.3, 131.1, 131.5, 133.2, 134.0, 134.8, 224
1H NMR, 500 MHz (CDCl3 + DMSO-d6) δ 6.15 (d, J = 8.4 Hz, 2H),
177 6.55–6.79 (m, 15H), 6.99 (d, J = 7.5 Hz, 2H), 8.84 (brs, OH, 1H): 13C
178 NMR (125 MHz, CDCl3/DMSO-d6) δ 115.2, 126.7, 127.1, 128.1, 128.2,
179 128.5, 129.1, 130.2, 131.1, 136.7, 146.8, 158.1: MS (m/z, %): 388 (M+
180 100).
,
136.9, 138.4, 146.5 MS (m/z, %): 422 (M+, 100).
225
181 5.2.4. (Table 1, 4e) 2-(4-methoxyphenyl)-1,4,5-triphenyl-1H-imidazole
182
1H NMR, 500 MHz (CDCl3 + DMSO-d6) δ 3.80 (s, 3H), 6.80 (d, J =
5.2.11. (Table 1, 4q) 2-(furan-2-yl)-1,4,5-triphenyl-1H-imidazole
226
183 8.6 Hz, 2H), 7.08 (d, J = 7.0 Hz, 2H), 7.15 (d, J = 7.0 Hz, 2H), 7.21–
184 7.33 (m, 9H), 7.41 (d, J = 8.6 Hz, 2H), 7.64 (d, J = 7.5 Hz, 2 H): 13C
185 NMR (125 MHz, CDCl3) δ 55.6, 114.0, 127.0, 127.9, 128.4, 128.6, 128.7,
186 128.9, 129.5, 130.9, 137.4, 142.2, 160.2: MS (m/z, %): 402 (M+, 100).
1H NMR, 500 MHz (CDCl3 + DMSO-d6) δ 6.45 (d, J = 3.4 Hz, 1H), 227
6.90 (t, J = 4.2 Hz, 1H), 7.17 (t, J = 4.2 Hz, 1H), 7.23–7.27 (m, 7H), 228
7.42–7.50 (m, 8H): 13C NMR (125 MHz, CDCl3/DMSO-d6) δ 126.2, 229
127.1, 127.4, 127.9, 128.3, 129.0, 129.3, 130.0, 130.3, 130.4, 130.8, 230
131.9, 132.1, 133.7, 134.9, 136.9, 137.6, 142.2: MS (m/z, %): 378 (M+), 231
187 5.2.5. (Table 1, 4h) methyl-4-(1,4,5,-triphenyl-1H-imidazole-2-yl)
188 benzoate
189
165, (100).
232
1H NMR, 500 MHz (CDCl3 + DMSO-d6) δ 3.93, (s, 3H), 7.08 (d, J =
6. Uncited references
2Q383
190 7.2 Hz, 2H), 7.16 (d, J = 6.7 Hz, 2H), 7.26–7.37 (m, 9H), 7.55 (d, J =
191 8.3 Hz, 2H), 7.63 (d, J = 7.2 Hz, 2H), 7.94 (d, J = 8.3 Hz, 2H): 13C NMR
192 (125 MHz, CDCl3) δ 52.5, 127.4, 127.9, 128.6, 128.7, 128.8, 129.1,
193 129.7, 129.8, 131.5, 132.0, 145.9, 167.0; MS (m/z, %): 430 (M+, 100).
[48,49,51,52,53,54,55,56,57]
234
References
235
236
194 5.2.6. (Table 1, 4i) 2-(4-nitrophenyl)-1,4,5-triphenyl-1H-imidazole
195
UNCORRECTED PR
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197 (m, 4H), 8.12 (d, J = 8.6 Hz, 2 H): 13C NMR (125 MHz, CDCl3) δ 123.8,
198 127.6, 127.8, 128.6, 128.7, 128.9, 129.0, 1129.5, 129.6, 130.0, 131.4,
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Please cite this article as: N. Aziizi, et al., Journal of Molecular Liquids (2014), http://dx.doi.org/10.1016/j.molliq.2014.03.013