ZnO as an efficient and inexpensive catalyst for one pot synthesis of 2, 4, 5 -Triphenyl-1H - Imidazole derivatives at room temperature

Article abstract of DOI:10.1155/2011/759706

An improved and rapid one pot synthesis of 2,4,6-triphenyl- 1H-imidazoles on condensation with benzil, aromatic aldehyde and NH4OAc has been carried out using ZnO as an efficient and inexpensive catalyst in high yield at room temperature. The short reaction time, good yields (60-93%), environmental friendly procedure, mild reaction condition and convenient operation are important advantage of these synthetic methods.

Full text of DOI:10.1155/2011/759706

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2011, 8(3), 1339-1345
http://www.e-journals.net
ZnO as an Efficient and Inexpensive Catalyst
for One Pot Synthesis of 2, 4, 5 -Triphenyl-
H - imidazole Derivatives at Room Temperature
1
*
BABASAHEB P. BANDGAR , BALIRAM S. HOTE,
BALAJI L. KORBAD and SACHIN A. PATIL
*
Medicinal Chemistry Research Laboratory
School of Chemical Sciences, Solapur University, Solapur, India
Organic Chemistry Research Laboratory, School of Chemical Sciences
Swami Ramanand Teerth Marathwada University, Nanded, India
bandgar_bp@yahoo.com
Received 3 November 2010; Accepted 20 January 2011
Abstract: An improved and rapid one pot synthesis of 2,4,6-triphenyl-
1
H-imidazoles on condensation with benzil, aromatic aldehyde and NH OAc
4
has been carried out using ZnO as an efficient and inexpensive catalyst in high
yield at room temperature. The short reaction time, good yields (60-93%),
environmental friendly procedure, mild reaction condition and convenient
operation are important advantage of these synthetic methods.
Keywords: Benzil, NH OAc, Aromatic aldehyde, ZnO, One pot synthesis
4
Introduction
The importance of imidazoles in biological systems has attracted much interest due to their
chemical and biochemical properties. Compounds with imidazole ring system have many
1
pharmacological properties and play an important role in biochemical process . The structures
of trisubstituted imidazoles are prevalent in natural products and pharmacologically active
2
compounds, such as p38 kinase inhibitor I (SB 203580) and cyclooxygenase-2 (COX-2)
3
inhibitor II, (Figure 1) fungicides and herbicides , plant growth regulators and therapeutic
4
5
6
agents . Recent advances in green chemistry and organometallic chemistry have extended the
boundary of imidazoles to the synthesis and application of a large class of imidazoles as ionic
7,8
liquids and imidazole related N-heterocyclic carbenes (NHC) .
There are several methods reported in literature for the synthesis of imidazoles such as
9
hetero-cope rearrangement , four component condensation of arylglyoxals, primary amines,
1
0
carboxylic acids and isocyanides on Wang resin , reaction of N-(2-oxo)-amides with ammonium

ZnO as an Efficient and Inexpensive Catalyst for One Pot Synthesis
1340
11
12
trifluroacetate , 1,2-aminoalcohols in the presence of PCl , diketones, aldehyde, amine
5
13
14
and ammonium acetate in phosphoric acid , in acetic acid , organo catalyst in acetic acid
15
16
17
as well as H SO4 , DMSO . Several microwave (MW) assisted syntheses of imidazoles
2
from 1, 2-diketones and aldehydes in the presence of a variety of catalysts have been
20
1
8
19
recently reported. These include MW/silica-gel , MW/silica-gel/ H-Y , MW/Al O
,
3
2
21
22
MW/CH COOH , in DMF . The condensation of α-hydroxy ketones with aldehydes and
3
ammonium acetate on solid supported silica gel or alumina in the presence of MW has been
23
reported recently .
Designing of new specific catalysts and exploring their catalytic activity has caused
profound effects in optimizing the efficiency of a wide range of organic synthesis.
Development of such catalysts has resulted in more economical and environmentally
24
friendly chemistry through replacing nonselective, unstable, or toxic catalysts . Surface of
metal oxides exhibit both lewis acid and lewis base characters. This is characteristic of many
metal oxides, especially TiO , Al O , ZnO, etc. and they are excellent adsorbents for a wide
2
2
3
25
variety of organic compounds and increase reactivity of the reactants . ZnO is certainly one
of the most interesting of metal oxides, because it has surface properties which suggest that a
26
very rich organic chemistry may occur there .
3
F C
N
N
N
N
O
N
S
N
H
F
2 2
SO NH
I
II
Figure 1
Many of the synthetic protocols for imidazoles reported so far suffer from one or more
disadvantages such as harsh reaction conditions, poor yields, prolonged time period, use of
hazardous and often expensive acid catalysts. Moreover, the syntheses of these heterocycles have
been usually carried out in polar solvents such as ethanol, methanol, acetic acid, DMF and
DMSO leading to complex isolation and recovery procedures. These processes also generate
waste containing catalyst and solvent, which have to be recovered, treated and disposed off.
CHO
O
N
ZnO (5 mol %)
4
NH OAc
+
+
RT, MeCN,
0 - 90 min
6
R
N
H
O
R
1
2
3a-o
3
3
3
3
3
a: R = H
d: R = 2 - Cl
3b: R = 4 - Me
3e: R = 4 - Cl
3h: R = 4 - OMe 3i: R = 4 - OH
3c: R = 4 - Br
3f: R = 3 - NO
2
g: R = 2 - OH
j: R = 3, 4 - (OMe)
m: R = 2 - F
2
3k: R = 2 - NO
3n: R = 4 - F
2
3l: R = 4 - NO
3o: R = 2 - Me
2
Scheme 1

1
341
B. P. BANDGAR et al.
Experimental
Melting points were recorded in open capillaries with super fit melting point apparatus and
1
were uncorrected. H NMR spectra were recorded on 300 MHz Bruker FT-NMR
spectrometer using tetramethylsilane as internal standard and chemical shifts are reported in
1
3
δ units and the coupling constant (J) are reported in hertz. C NMR spectra were recorded
on a Bruker DRX-300 Avance spectrometer. Mass spectra were recorded on Bruker
daltonics data analysis 3.4. All chromatographic purification was performed with silica gel
(
(
100 - 200 mesh), whereas all TLC (silica gel) developments were performed on silica gel
Merck Kiesel 60F254, 0.2 mm thickness) sheets. All reagents and solvents were of
commercial quality and were used as supplied unless otherwise stated. Yields reported are
isolated yield of the compounds.
General procedure for synthesize of 2,4,5–triphenyl-1H-imidazole derivatives (3a-j)
A mixture of benzil (1 mmol), aldehyde (1 mmol), NH OAc (5 mmol) and ZnO (5 mol%) in
4
acetonitrile (10 mL) was stirred at room temperature. After completion of the reaction
(
(
TLC analysis), it was diluted with water (10 mL) and extracted with dichloromethane
25 mL). The organic layer was dried (Na SO ), evaporated and purified by chromatography
2
4
by using chloroform to give the products in 60 - 93% yields.
Selected spectral data of the products
2
,4,5-Triphenyl-1H-imidazole (Table 2 entry 1)
o
-1
1
Solid; m.p. 267-269 C; IR (KBr) ν = 3434, 2993, 2470, 1638, 1216 cm ; H NMR
13
(
300 MHz, CDCl ): δ 12.61 (s, 1H), 7.42 - 8.12 (m, 15H); C NMR (CDCl ): δ 136.53,
3
3
1
5
29.14, 128.95, 127.23, 122.14; EIMS: m/z = 296. Anal. Calcd. for C H N : C, 85.11; H,
.44; N, 9.45. Found: C, 85.13; H, 5.28; N, 9.35.
21 16 2
4
,5–Dipheny-2-p-tolyl-1H-imidazole (Table 2 entry 2)
o
-1 1
Solid; m.p. 230-231 C; IR (KBr) ν = 3405, 3033, 1602, 1493, 1449 cm ; H NMR
(300
(s,
MHz, CDCl ): δ 12.60 (s, 1H), 7.98 (d, 2H, J = 8.4 Hz), 7.20 - 7.56 (m, 12H), 2.23
3
1
3
3
H); C NMR (CDCl ): δ 145.53, 137.65, 136.82, 135.24, 131.14, 129.23, 128.65, 128.35,
3
128.32, 127.65, 127.65, 127.08, 126.43, 125.35, 20.81; EIMS: m/z = 310. Anal. Calcd. for
C H N : C, 85.13; H, 5.83; N, 9.03. Found: C, 85.17; H, 5.85; N, 9.06.
2
2
18
2
2
-(4-Bromophenyl)-4,5-diphenyl-1H-imidazole (Table 2 entry 3)
o
-1 1
Solid; m.p. 248-250 C; IR (KBr) ν = 3400, 3060, 1601, 1482, 1450, 1429 cm ; H NMR
(
300 MHz, CDCl ): δ 12.79 (s, 1H), 8.04 (d, 2H, J = 8.4 Hz), 7.68 (d, 2H, J = 8.4 Hz),
3
13
7
1
.55 - 7.23 (m, 10H); C NMR (CDCl ): δ 144.34, 137.34, 134.90, 131.61, 130.83, 129.62,
3
28.64, 128.33, 128.10, 127.63, 127.13, 126.14, 121.33; EIMS: m/z = 385 (M+1). Anal.
Calcd. for C H BrN : C, 67.21; H, 4.03; Br, 21.29; N, 7.47. Found: C, 67.25; H, 4.08; Br,
2
2
1
15
2
1.31; N, 7.45.
2
-(2–Chlorophenyl)-4,5–diphenyl-1H-imidazole (Table 2 entry 4)
o
-1
1
Solid; m.p. 186-188 C; IR (KBr) ν = 3434, 2993, 2470, 1638, 1216 cm ; H NMR
(
300 MHz, CDCl ): δ 12.5 (s, 1H), 8.03 (dd, 1H, J = 8.7 Hz), 7.58 (d, 2H, J = 8 Hz), 7.47
3
13
(
dd, 1H, J = 9 Hz), 7.27 - 7.37 (m, 10H); C NMR (CDCl ): δ 142.25, 130.54, 130.15,
3
1
29.67, 128.83, 128.65, 128.47, 127.23, 126.90, 126.51, 125.62, 125.44; EIMS: m/z = 340
M+1). Anal. Calcd. for C H ClN : C, 76.24; H, 4.57; Cl, 10.72; N, 8.47. Found: C, 76.27;
(
H, 4.62; Cl, 10.68; N, 8.52.
21
15
2

ZnO as an Efficient and Inexpensive Catalyst for One Pot Synthesis
1342
2
-(4–Chlorophenyl)-4,5–diphenyl–1H-imidazole (Table 2 entry 5)
o
-1 1
Solid; m.p. 248-250 C; IR (KBr) ν = 3405, 3060, 1603, 1485, 1448, 1433 cm ; H NMR
13
(
CDCl ): δ 12.79 (s, 1H), 7.21 - 7.56 (m, 12H), 8.11 (d, 2H, J = 8.8 Hz); C NMR (CDCl ):
3
3
δ 144.33, 137.24, 134.92, 132.54, 130.84, 130.81, 129.14, 128.73, 128.54, 128.40, 128.31,
1
28.14, 127.06, 126.55, 126.24; EIMS: m/z = 340 (M+1). Anal. Calcd. for C H ClN : C,
6.24; H, 4.57; Cl, 10.72; N, 8.47. Found: C, 76.28; H, 4.60; Cl, 10.68; N, 8.50.
2
1
15
2
7
2
-(3-Nitrophenyl)-4,5-diphenyl–1H-imidazole (Table 2 entry 6)
o
-1
1
Solid; m.p. 252-254 C;IR (KBr) ν = 3382, 3064, 1605, 1519, 1348 cm ; H NMR
(
(
300 MHz, CDCl ): δ 13.10 (s, 1H), 8.96 (t, 1H, J = 2.0 Hz), 8.50 - 8.55 (m, 1H), 8.15-8.25
3
13
m, 1H), 7.78 (t, 1H, J = 8 Hz), 7.24 - 7.60 (m, 10H); C NMR (CDCl ): δ 148.36, 143.25,
3
1
37.55, 134.52, 131.14, 130.53, 130.32, 129.03, 128.64, 128.30, 128.21, 128.00, 127.62,
22.55, 119.44; EIMS: m/z = 350. Anal. Calcd. for C H N O : C, 73.89; H, 4.43; N, 12.31;
1
O, 9.97. Found: C, 73.94; H, 4.46; N, 12.29; O, 9.94.
21
15
3
2
2
-(4,5–Diphenyl-1H–imidazol–2-yl)phenol (Table 2 entry 7)
o
-1
1
Solid; m.p. 117-119 C; IR (KBr) ν = 3438, 2985, 2970, 1625, 1226 cm ; H NMR
(
300 MHz, CDCl ): δ 12.62 (s, 1H), 8.03 (dd, 2H, J = 8.7 Hz), 7.59 (d, 2H, J = 8 Hz), 7.49
3
13
(
s, 1H), 7.27 - 7.34 (m, 10H); C NMR (CDCl ): δ 147.62, 133.15, 130.25, 129.53, 128.17,
3
1
5
21.95, 118.56, 116.48; EIMS: m/z = 321 (M+1). Anal. Calcd. for C H N O: C, 80.75; H,
.16; N, 8.97; O, 5.12. Found: C, 80.78; H, 5.14; N, 9.02; O, 5.14.
21 16 2
2
-(4-Methoxyphenyl)-4,5–diphenyl-1H-imidazole (Table 2 entry 8)
o
-1
1
Solid; m.p. 220-222 C; IR (KBr) ν = 3428, 2893, 2465, 1636, 1216 cm ; H NMR
(
300 MHz, CDCl ): δ 12.52 (s, 1H), 8.03 (d, 2H, J = 8.8 Hz), 7.55 - 7.59 (m, 10H),
3
13
6
1
.94 (d, 2H, J = 8.8 Hz), 3.85 (s, 3H); C NMR (CDCl ): δ 159.17, 145.75, 132.83,
3
27.64, 127.45, 126.53, 126.34, 122.73, 113.27, 54.63; EIMS: m/z = 326. Anal. Calcd.
for C H N O: C, 80.96; H, 5.56; N, 8.58; O, 4.90. Found: C, 80.99; H, 5.59; N, 8.56;
2
2
18
2
O, 4.93.
4
-(4,5-Diphenyl-1H–imidazol–2-yl)phenol (Table 2 entry 9)
o
-1 1
Solid; m.p. 202-204 C; IR (KBr) ν = 3428, 3215, 1602, 1532 cm ; H NMR (300 MHz,
CDCl ): δ 12.51 (s, 1H), 7.2 - 7.52 (m, 10H), 6.99 (d, 2H, J = 7.8 Hz), 6.89 (d, 2H, J = 7.5 Hz);
3
1
3
C NMR (CDCl ): δ 156.55, 145.46, 129.18, 128.37, 127.93, 126.92, 124.74, 119.08,
3
116.54, 112.82. EIMS: m/z = 321. Anal. Calcd. for C H N O: C, 80.75; H, 5.16; N, 8.97;
O, 5.12. Found: C, 80.80; H, 5.19; N, 9.03; O, 5.17.
21
16
2
2
-(3,4-Dimethoxyphenyl)-4,5-diphenyl-1H-imidazole (Table 2 entry 10)
o
-1 1
Solid; m.p. 210-212 C; IR (KBr) ν = 3431, 2987, 2893, 2465, 1636, 1216 cm ; H NMR
300 MHz, CDCl ): δ 12.48 (s, 1H), 8.05 (d, 2H, J = 8.7 Hz), 7.28. - 7.61 (m, 10H), 6.95 (d, 1H),
(
3
13
3
.85 (s, 6H); C NMR (CDCl ): δ 150.35, 147.64, 144.82, 129.57, 129.33, 129.30, 129.34,
3
1
m/z = 356. Anal. Calcd. for C H N O : C, 77.51; H, 5.66; N, 7.86; O, 8.98. Found: C,
28.83, 128.81, 127.58, 127.56, 133.14, 124.21, 120.83, 115.81 112.34, 56.24; EIMS:
23
20
2
2
7
7.56; H, 5.69; N, 7.90; O, 8.94.
Results and Discussion
Having established the advantages of ZnO as catalyst, bearing in mind that solvents can also
effect the chemical reaction, we continued to optimize the process by varying the solvents.

1
343
B. P. BANDGAR et al.
such as acetonitrile, THF, ethanol, THF/water (1/1), acetonitrile/water (1/1), ethanol/water (1/1)
and toluene (shown in Table 1) were chosen as the medium for a comparison. It was found that
compound 1 (1 mmol), 2 (1 mmol) and NH OAc were mixed together with ZnO (5 mol%) and
4
solvent (5 mL) stirred at room temperature. It was found that acetonitrile (entry 1, Table 1)
gave the highest yield of the desired product. When other mentioned solvents (Table 1) were
used, the reaction suffered many disadvantages such as more reaction time and lower yields.
Table 1. Optimization of reaction condition for synthesis of 2, 4, 5-triphenyl 1H-imidazole
derivatives using 5 mol% ZnO catalyst
a
Yields , %
Entry
Solvent
Acetonitrile
THF
Time, h
1
2
3
4
5
6
7
1
4
6
5
4
6
9
93
60
54
46
58
68
39
Ethanol
THF/Water
Acetonitrile/Water
Ethanol/Water
Toluene
a
Isolated yields
The progress of reaction by using solvents revealed that when the reaction was
performed in acetonitrile, it proceeded much faster than in other solvents; to afford entry 3 in
93% yield (Table 2). A similar reaction was also carried out in solvents toluene in (Table 1),
in this case, the reaction took longer reaction time with less yields.
Table 2. Synthesis of 2,4,5-tripheny-1H-imidazole derivatives in the presences of ZnO catalyst
b
Entry
R
Product
3a
Time, min
65
75
Yield , %
75
63
1
2
3
4
5
6
7
8
9
H
4-Me
4-Br
3b
3c
60
62
64
70
93
84
89
85
2-Cl
4-Cl
3d
3e
3-NO2
2-OH
3-OMe
4-OH
3,4-(OMe)2
2-NO2
4- NO2
2-F
3f
3g
80
90
71
69
3h
3i
3j
85
78
68
70
1
1
1
1
1
1
0
1
2
3
4
5
3k
3l
62
65
74
74
3m
3n
3o
60
58
81
78
4-F
2-Me
b
93
65
All yields refer to isolated products
The synthetic strategy is based on the condensation of 1, 2-diphenylethanedienones with
variety of aldehydes and amines in the presence of an excess of NH OAc, resulting in
4
2, 4, 5-tripheny l-1H - imidazole derivatives 3a-o by using 5 mol% of ZnO catalyst. Initially,
benzil 1 in acetonitrile was treated with an equimolar quantity of variety of aromatic
banzaldehyde, excess of NH OAc stirred at room temperature for 60 - 90 min to furnish 2, 4,
4
5
- triphenyl -1H - imidazole derivatives, 3a-o (Table 2) in 63 - 93% yields.

ZnO as an Efficient and Inexpensive Catalyst for One Pot Synthesis
1344
To examine the scope and limitations of this reaction, we carried out the reaction of
various aromatic aldehydes including both electron donating and electron withdrawing
substituents in ortho, meta and para positions of benzaldehyde (Table 2). We found that the
reaction proceeded very efficiently in all cases and the reaction time decreased for aldehydes
containing electron withdrawing substitutents. The best result was obtained with
4-bromobenzaldehyde (93% yield, entry 3, Table 2) and the least yield (63%) was obtained
from 4-methyl benzaldehyde after stirring for 75 min (Table 2, entry 2).
Conclusion
We have reported an efficient procedure for the synthesis of 2,4,5-triphenyl-1H-imidazole
3
a-o derivatives using ZnO as a reusable, non-toxic, non-corrosive, inexpensive and
commercially available heterogeneous catalyst. The method also offers some other
advantages such as clean reaction, low loading of catalyst, high yields of products, short
reaction times and use of various substrates, which make it a useful and attractive strategy
for the synthesis of 2,4,5-triphenyl-1H-imidazole derivatives.
Acknowledgment
BSH acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi,
India for financial support.
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Hindawi Publishing Corporation
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Volume 2014
Volume 2014
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Journal of
The Scientific
Analytical Methods
in Chemistry
World Journal
Hindawi Publishing Corporation
Hindawi Publishing Corporation
http://www.hindawi.com
http://www.hindawi.com
Volume 2014
Volume 2014
Journal of
International Journal of
International Journal of
Journal of
Bioinorganic Chemistry
Spectroscopy
Inorganic Chemistry
Electrochemistry
Applied Chemistry
and Applications
Hindawi Publishing Corporation
http://www.hindawi.com
Hindawi Publishing Corporation
Hindawi Publishing Corporation
Hindawi Publishing Corporation
Hindawi Publishing Corporation
Volume 2014
http://www.hindawi.com
Volume 2014
http://www.hindawi.com
Volume 2014
http://www.hindawi.com
Volume 2014
http://www.hindawi.com
Volume 2014
Journal of
Chromatography
Journal of
International Journal of
Journal of
Theoretical Chemistry
Catalysts
Research International
Chemistry
Spectroscopy
Hindawi Publishing Corporation
http://www.hindawi.com
Hindawi Publishing Corporation
http://www.hindawi.com
Hindawi Publishing Corporation
http://www.hindawi.com
Hindawi Publishing Corporation
http://www.hindawi.com
Hindawi Publishing Corporation
http://www.hindawi.com
Volume 2014
Volume 2014
Volume 2014
Volume 2014
Volume 2014