Acetic acid-promoted condensation of o-phenylenediamine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles under microwave irradiation

Article abstract of DOI:10.2298/JSC090901096A

An efficient and simple procedure was developed for the green synthesis of various 2-aryl-1-(arylmethyl)-1 H-benzimidazoles in high yields by acetic acid-promoted condensation of o-phenylenediamine with aldehydes in air under microwave irradiation and transition metal catalyst-free conditions. 2010 Copyright (CC) SCS.

Full text of DOI:10.2298/JSC090901096A

J. Serb. Chem. Soc. 75 (9) 1181–1189 (2010)
JSCS–4041
UDC 547.292+547.586.2+547.53.024:
54–732+537.5
Original scientific paper
Acetic acid-promoted condensation of o-phenylenediamine with
aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles
under microwave irradiation
1
1
2
*
DAVOOD AZARIFAR , MOJGAN PIRHAYATI , BEHROOZ MALEKI ,
MEHRANGIZ SANGINABADI1 and RAZIEH NEJAT YAMI1
1Faculty of Chemistry, Bu-Ali Sina University, Hamadan-65178 and 2Department of
Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar-397, Iran
(Received 1 September 2009, revised 30 April 2010)
Abstract: An efficient and simple procedure was developed for the green syn-
thesis of various 2-aryl-1-(arylmethyl)-1H-benzimidazoles in high yields by ace-
tic acid-promoted condensation of o-phenylenediamine with aldehydes in air
under microwave irradiation and transition metal catalyst-free conditions.
Keywords: 2-aryl-1-(arylmethyl)-1H-benzimidazoles; o-phenylenediamine; alde-
hydes; microwave irradiation, acetic acid.
INTRODUCTION
The benzimidazole nucleus is of significant importance in medicinal che-
mistry and many benzimidazole-containing compounds exhibit important biolo-
1–4
gical activities, i.e., as selective neuropeptide YY1 receptor antagonists,
5-li-
5
poxygenase inhibitors for use as novel anti-allergic agents, factor Xa (FXa) in-
hibitors, poly (ADP-ribose) polymerase (PARP) inhibitors, and as human cyto-
megalovirus (HCMV) inhibitors. In addition, several substituted benzimidazole
6
7
8
derivatives have been recently reported to have commercial applications in vete-
rinarian medicine, i.e., as anthelmintic agents, and in diverse human therapeutic
9
areas, such as treatment of ulcers and as antihistaminic. In the light of the affi-
nity they display towards a variety of enzymes and protein receptors, medicinal
chemists would certainly classify them as “privileged sub-structures” for drug de-
10
sign. Therefore, the clinical significance of this class of compounds stimulated
interest in the synthesis of novel ring systems agents, with retention of the core
imidazole moiety.
Traditionally, the synthesis of benzimidazoles involves the condensation of
11–13
o-phenylenediamine with aldehydes,
and carboxylic acids or their deriva-
*Corresponding author. E-mail: azarifar@basu.ac.ir
doi: 10.2298/JSC090901096A
1181
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1182
AZARIFAR et al.
14–20
tives (nitriles, amidates, orthoesters) under harsh dehydrating conditions.
Benzimidazoles have also been prepared on a solid-phase to provide a combi-
21,22
natorial approach.
The most popular strategies for their synthesis utilize o-
nitroanilines as intermediates or resort to direct N-alkylation of an unsubstituted
23
benzimidazole. A number of synthetic methods that involve intermediate o-nit-
roanilines have evolved to include the synthesis of benzimidazoles on solid sup-
24–29
ports.
Another reported approach to these compounds is the reaction of
o-phenylenediamine with aldehydes in the presence of catalysts under various
30–41
reaction conditions.
Recently, a one-pot, solvent-free synthesis of biolo-
42
gically active benzimidazole derivatives using a simple grinding method, and
another under heterogeneous catalysis of amberlite IR-120 have been reported.
43
RESULTS AND DISCUSSION
In continuation of previously reported research on the use of acetic
acid in various transformations,44–46 herein, a very simple and selective
synthesis of 2-aryl-1-(arylmethyl)-1H-benzimidazoles 2a–m by acetic acid-
-promoted condensation of o-phenylenediamine with aldehydes 1a–m both under
microwave irradiation and conventional thermal heating in air is reported (Sche-
me 1, Table I).
Scheme 1. The synthesis of the title compounds.
The structural elucidations of the products were based on their spectral (IR,
1
13
H- and C-NMR and mass) data as given below.
1-Benzyl-2-phenyl-1H-benzimidazole (2a). IR (KBr, cm ): 3031 (C–H
–1
stretching of aromatic ring), 2926 (C–H stretching of aliphatic), 1594 (C=N
stretching of imidazole ring), 1549, 1502, 1549, 1448 (C=C stretching of aro-
1
matic ring), 1371 (C–N stretching of imidazole ring). H-NMR (90 MHz, CDCl ,
3
13
δ / ppm): 5.34 (2H, s, –CH –), 7.02–7.28 (15H, m, Ar–H). C-NMR (22.5 MHz,
2
CDCl , δ / ppm): 47.80, 110.32, 119.41, 122.23, 125.72, 127.31, 128.46, 128.78,
3
128.80, 129.42, 135.51, 135.84, 142.62, 149.82 (C=N), 153.70. MS (m/z): 284
+
(M ).
–1
1-(4-Methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole (2b). IR (KBr, cm ):
3024 (C–H stretching of aromatic ring), 2930 (C–H stretching of aliphatic), 1623
(C=N stretching of imidazole ring), 1520, 1488 (C=C stretching of aromatic
1
ring), 1284 (C–N stretching of imidazole ring). H-NMR (90 MHz, CDCl , δ /
3
/ ppm): 2.45 (3H, s, CH ), 2.51 (3H, s, CH ), 5.53 (2H, s, –CH –), 7.10–7.95
3
3
2
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SYNTHESIS OF 2-ARYL-1-(ARYLMETHYL)-1H- BENZIMIDAZOLES
1183
13
(12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ / ppm): 21.0, 21.3, 48.2, 110.3,
3
119.7, 122.5, 122.7, 125.7, 127.0, 128.9, 129.3, 129.5, 133.2, 136.1, 137.4,
+
139.8, 143.1, 154.2 (C=N). MS (m/z): 312 (M ).
TABLE I. Acetic acid-promoted synthesis of 2-aryl-1-(arylmethyl)-1H-benzimidazoles
M.p., °C
Producta
R
Timeb, min
Yieldb,c, %
Found
Reported
2a
2b
2c
2d
2e
2f
2g
2h
2i
C6H5
25 (4)
60 (6)
30 (5)
40 (5)
30 (7)
35 (8)
30 (6)
50 (8)
35 (5)
50 (5)
20 (4)
35 (6)
35 (8)
92 (97)
64 (82)
90 (96)
80 (95)
60 (85)
58 (78)
82 (85)
70 (80)
92 (98)
70 (75)d
92 (95)
68 (86)
52 (75)
132–134
126–128
130–131
154–155
250–253
205–208
138–140
158–159
254–256
96–98
13232
4-MeC6H4
4-MeOC6H4
2-MeOC6H4
4-HOC6H4
2-HOC6H4
4-ClC6H4
2-ClC6H4
4-Me2NC6H4
2-Furyl
12632
13132
15132
254–25641
207–20841
13732
15532
25232
2j
2k
2l
9632
4-CNC6H4
4-NO2C6H4
2-NO2C6H4
190–191
119–120
169–170
187–18841
11832
2m
168–17033
aThe products were characterized by their physical properties and spectral analysis and compared with authen-
b
tic samples; the reaction times and yields obtained using microwave irradiation are shown in the parenthesis;
c
d
yield isolated; the product 3j was isolated in 20 (thermal) and 25 % (microwave irradiation) yields. M.p.
122–124 °C (lit.:33 120 °C)
1-(4-Methoxybenzyl)-2-(4-methoxyphenyl)-1H-benzimidazole (2c). IR (KBr,
–1
cm ): 3030 (C–H stretching of aromatic ring), 2932 (C–H stretching of alipha-
tic), 1609 (C=N stretching of imidazole ring), 1538, 1460 (C=C stretching of aro-
1
matic ring), 1244 (C–N stretching of imidazole ring). H-NMR (90 Mz, CDCl ,
3
δ / ppm): 3.79 (3H, s, OCH ), 3.89 (3H, s, OCH ), 5.34 (2H, s, –CH –), 6.92–
3
3
2
13
–7.78 (12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ / ppm): 47.8, 55.2, 55.3,
3
110.3, 114.2, 114.4, 119.6, 122.5, 122.7, 127.2, 128.4, 130.6, 136.1, 143.2, 154.0
+
(C=N), 159.1, 160.9. MS (m/z): 344 (M ).
1-(2-Methoxybenzyl)-2-(2-methoxyphenyl)-1H-benzimidazole (2d). IR (KBr,
–1
cm ): 3063 (C–H stretching of aromatic ring), 2961 (C–H stretching of alipha-
tic), 1600 (C=N stretching of imidazole ring), 1583, 1454 (C=C stretching of aro-
1
matic ring), 1258 (C–N stretching of imidazole ring); H-NMR (90 MHz, CDCl ,
3
δ / ppm): 3.46 (3H, s, OCH ), 3.64 (3H, s, OCH ), 5.21 (2H, s, –CH –), 6.64–
3
3
2
13
–7.81 (12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ / ppm): 43.2, 55.0, 55.1,
3
109.8, 110.5, 110.6, 119.7, 120.2, 120.6, 121.8, 122.3, 124.3, 127.4, 128.2,
+
131.3, 132.1, 135.3, 143.1, 152.4 (C=N), 156.3, 157.3. MS (m/z): 344 (M ).
4-{[2-(4-Hydroxyphenyl)-1H-benzimidazol-1-yl]methyl}phenol (2e). IR (KBr,
–1
cm ): 3348 (O–H stretching of phenyl ring), 3002 (C–H stretching of aromatic
ring), 2925 (C–H stretching of aliphatic), 1597 (C=N stretching of imidazole
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AZARIFAR et al.
ring), 1515, 1412 (C=C stretching of aromatic ring), 1266 (C–N stretching of
1
imidazole ring). H-NMR (90 MHz, DMSO-d , δ / ppm): 5.32 (2H, s, –CH –),
6
2
6.78–7.80 (12H, m, Ar–H), 9.33 (1H, brs, OH), 9.89 (1H, brs, OH). MS (m/z):
+
316 (M ).
2-{[2-(2-Hydroxyphenyl)-1H-benzimidazol-1-yl]methyl}phenol (2f). IR (KBr,
–1
cm ): 3384 (O–H stretching of phenyl ring), 3010 (C–H stretching of aromatic
ring), 2910 (C–H stretching of aliphatic), 1600 (C=N stretching of imidazole
ring), 1460, 1425 (C=C stretching of aromatic ring), 1298 (C–N stretching of
1
imidazole ring). H-NMR (90 MHz, DMSO-d6, δ / ppm): 5.58 (2H, s, –CH –),
2
6.18–7.34 (12H, m, Ar–H), 9.48 (1H, brs, OH), 10.04 (1H, brs, OH). MS (m/z):
+
316 (M ).
1-(4-Chlorobenzyl)-2-(4-chlorophenyl)-1H-benzimidazole (2g). IR (KBr,
–1
cm ): 3050 (C–H stretching of aromatic ring), 2920 (C–H stretching of ali-
phatic), 1546 (C=N stretching of imidazole ring), 1522, 1441 (C=C stretching of
1
aromatic ring), 1346 (C–N stretching of imidazole ring). H-NMR (90 MHz,
13
CDCl , δ / ppm): 5.49 (2H, s, –CH –), 7.14–8.19 (12H, m, Ar–H). C-NMR
3
2
(22.5 MHz, CDCl , δ / ppm): 47.6, 110.3, 120.1, 123.2, 123.4, 127.2, 128.4,
3
129.1, 129.2, 130.3, 133.7, 134.6, 135.7, 136.2, 142.9, 152.8 (C=N); MS (m/z):
+
353 (M ).
1-(2-Chlorobenzyl)-2-(2-chlorophenyl)-1H-benzimidazole (2h). IR (KBr,
–1
cm ): 3059 (C–H stretching of aromatic ring), 2924 (C–H stretching of alipha-
tic), 1612 (C=N stretching of imidazole ring), 1512, 1418 (C=C stretching of aro-
1
matic ring), 1396 (C–N stretching of imidazole ring). H-NMR (90 MHz, CDCl ,
3
13
δ / ppm): 5.33 (2H, s, –CH –), 6.57–7.85 (12H, m, Ar–H). C-NMR (22.5 MHz,
2
CDCl , δ / ppm): 45.6, 110.4, 120.3, 122.4, 123.3, 126.7, 127.0, 127.6, 128.8,
3
129.4, 129.3, 129.7, 131.2, 132.1, 132.3, 133.2, 134.1, 134.6, 142.8, 151.3
+
(C=N). MS (m/z): 353 (M ).
1-[4-(Dimethylamino)benzyl]-2-[4-(dimethylamino)phenyl]-1H-benzimidazole
–1
(2i). IR (KBr, cm ): 3029 (C–H stretching of aromatic ring), 2912 (C–H
stretching of aliphatic), 1590 (C=N stretching of imidazole ring), 1520, 1412
1
(C=C stretching of aromatic ring), 1348 (C–N stretching of imidazole ring). H-
-NMR (90 MHz, CDCl , δ / ppm): 2.84 (6H, s, NMe ), 2.92 (6H, s, NMe ), 5.42
3
2
2
13
(2H, s, –CH –), 6.68–7.03 (12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ /
2
3
/ ppm): 40.1, 40.4, 48.0, 110.4, 111.6, 112.6, 117.0, 119.1, 122.2, 124.2, 126.7,
+
130.3, 136.2, 143.0, 149.8, 151.1 (C=N), 155.2. MS (m/z): 370 (M ).
–1
2-(2-Furyl)-1-(2-furylmethyl)-1H-benzimidazole (2j). IR (KBr, cm ): 3020
(C–H stretching of aromatic ring), 2925 (C–H stretching of aliphatic), 1577
(C=N stretching of imidazole ring), 1512, 1470 (C=C stretching of aromatic
ring), 1328 (C–N stretching of imidazole ring), 1248 (C–O stretching of furyl
1
ring). H-NMR (90 MHz, CDCl , δ / ppm): 5.60 (2H, s, –CH –), 6.21–7.60
3
2
13
(10H, m, Ar–H). C-NMR (22.5 MHz, DMSO-d , δ / ppm): 41.6, 108.2, 109.8,
6
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SYNTHESIS OF 2-ARYL-1-(ARYLMETHYL)-1H- BENZIMIDAZOLES
1185
110.0, 110.4, 112.0, 112.8, 119.7, 122.8, 123.2, 135.3, 142.5, 142.9, 143.7,
+
145.3, 149.5 (C=N). MS (m/z): 264 (M ).
4-{[2-(4-Cyanophenyl)-1H-benzimidazol-1-yl]methyl}benzonitrile (2k). IR
–1
(KBr, cm ): 3061 (C–H stretching of aromatic ring), 2912 (C–H stretching of
aliphatic), 2227 (C–N stretching of phenyl ring) 1608 (C=N stretching of imi-
dazole ring), 1504, 1478, 1457 (C=C stretching of aromatic ring), 1386 (C–N
1
stretching of imidazole ring). H-NMR (90 MHz, CDCl , δ / ppm): 5.49 (2H, s,
3
13
–CH –), 7.21–7.72 (12H, m, Ar–H); C-NMR (22.5 MHz, CDCl , δ / ppm):
2
3
48.0, 110.2, 111.1, 112.3, 113.7, 117.9, 120.6, 123.5, 124.2, 126.6, 129.6, 132.5,
+
133.0, 134.1, 135.9, 141.1, 143.1, 151.7 (C=N). MS (m/z): 334 (M ).
–1
1-(4-Nitrobenzyl)-2-(4-nitrophenyl)-1H-benzimidazole (2l). IR (KBr, cm ):
3075 (C–H stretching of aromatic ring), 2926 (C–H stretching of aliphatic), 1614
(C=N stretching of imidazole ring), 1526, 1350 (–NO stretching of aromatic
2
ring), 1507, 1445 (C=C stretching of aromatic ring), 1390 (C–N stretching of
1
imidazole ring). H-NMR (90 MHz, CDCl , δ / ppm): 5.50 (2H, s, –CH –), 7.22–
3
2
13
–8.37 (12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ / ppm): 47.8, 110.2,
3
120.5, 123.6, 124.0, 124.5, 124.7, 126.6, 130.1, 135.6, 135.8, 142.5, 143.0,
+
147.5, 148.5, 151.2 (C=N); MS (m/z): 374 (M ).
–1
1-(2-Nitrobenzyl)-2-(2-nitrophenyl)-1H-benzimidazole (2m). IR (KBr, cm ):
3085 (C–H stretching of aromatic ring), 2964 (C–H stretching of aliphatic), 1611
(C=N stretching of imidazole ring), 1529, 1347 (–NO2 stretching of aromatic
ring), 1576, 1459, 1433 (C=C stretching of aromatic ring), 1314 (C–N stretching
1
of imidazole ring). H-NMR (90 MHz, CDCl , δ / ppm): 5.56 (2H, s,
3
13
–CH –), 6.59–7.64 (12H, m, Ar–H). C-NMR (22.5 MHz, CDCl , δ / ppm):
2
3
45.6, 110.2, 120.3, 123.0, 123.6, 124.8, 125.0, 125.5, 128.2, 128.7, 131.4, 131.8,
+
133.2, 134.1, 134.6, 143.0, 146.5, 148.7, 149.6 (C=N); MS (m/z): 374 (M ).
1
13
The H- and C-NMR spectra of the obtained products are in full conso-
nance with benzimidazole structures and their melting points are in agreement
13
with those reported, (Table I). It was observed that the reactions performed
under microwave irradiation were brought to completion in 4–12 min at the 60 %
power level. When these reactions were performed under reflux condition at 80
°C for the same time, lower yields of products were obtained, as given in Table I.
A possible mechanism proposed for these reactions is depicted in Scheme 2.
This mechanism probably involves an initial acetic acid-promoted condensation
of o-phenylenediamine with aldehydes 1a–m to yield a di-imine intermediate A
followed by cyclization to the 2-aryl-1-(arylmethyl)-1H-benzimidazoles 2a–m
through the intermediate B (path a). In order to confirm the involvement of the
diarylidene-o-phenylenediamine (A) as an intermediate, dibenzylidene-o-phenyl-
enediamine was prepared separately by the reaction of o-phenylenediamine with
two equimolar amounts of benzaldehyde in AcOH at 100 °C after 20 min. Mic-
rowave irradiation of purely separated dibenzylidene-o-phenylenediamine as a
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AZARIFAR et al.
test compound in acetic acid under the same conditions as used for the reactions
resulted merely in the formation of 1-benzyl-2-phenyl-1H-benzimidazole (2a).
This can be indicative that the reaction probably occurs via path a, with the
formation of A, followed by 1,3-hydride transfer, according to previous sugges-
32,36,41,47
tions.
However, the formation of 2-(2-furyl)benzimidazole 3j in minor
yield in the case of furylaldehyde (Table I) can be explained possibly through
path b involving the formation of dihydrobenzimidazole C intermediate followed
by dehydrative oxidation in air to yield 2-arylbenzimidazole 3, as suggested by
48
49
Xiangming and Zelenin et al. A direct oxidative condensation of aldoses with
diamines using molecular iodine in AcOH has already been reported for an im-
proved synthesis of aldo-benzimidazoles and aldo-naphthimidazoles, which sup-
50
ports the observations in this work. It is important to emphasize that, when
these reactions were conducted under nitrogen atmosphere, no formation of com-
pound 3 was detected and compounds 2a–m were isolated as the sole products in
slightly improved yields. This ratifies the role of air in partial oxidation of the
intermediate C to provide 1H-benzimidazole 3j.
Scheme 2. The suggested mechanism for the formation of the title compounds.
EXPERIMENTAL
Solvents, reagents, and chemical materials were obtained from Aldrich and Merck and
purified prior to use. Melting points were determined in open capillary tubes in a Stuart SMP3
apparatus and are uncorrected. Nuclear magnetic resonance spectra were recorded on a JEOL
FX 90Q using tetramethylsilane (TMS) as the internal standard. Infrared spectra were re-
corded on a Perkin Elmer GX FT IR spectrometer (KBr pellets). The microwave-assisted re-
actions were conducted in a Milstone CombiChem microwave synthesizer. In all irradiation ex-
periments, rotation of rotor, irradiation time, temperature and power were monitored with the
“Easy Wave” software package. Benzimidazoles were characterized based on their melting
points and IR, 1H- and 13C-NMR spectral data, which were compared with reported data.32,33,41
General procedure for the synthesis of 2-aryl-1-(arylmethyl)-1H-benzimidazoles (2a–m)
under microwave irradiation and thermal conditions
A mixture of o-phenylenediamine (0.11 g, 1.0 mmol) and aldehyde 1 (2.0 mmol) dis-
solved in glacial acetic acid (10 ml) was capped and irradiated in a Milstone CombiChem
microwave synthesizer for the appropriate time at 50 °C (Table I). The progress of the reac-
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SYNTHESIS OF 2-ARYL-1-(ARYLMETHYL)-1H- BENZIMIDAZOLES
1187
tion was monitored by intermittent rapid cooling of the mixture to r.t. every one minute and
analyzing by TLC (n-hexane/ethyl acetate, 2:8). After complete conversion of the substrate as
indicated by TLC analysis, the solvent was evaporated under reduced pressure to leave the
products 2a–m (and 3j), which were recrystallized from EtOH (96 %) (Table I). Similarly, in
a separate set of experiments, these reactions were all repeated in acetic acid under reflux con-
dition at 80 °C (Table I). Their melting points and yields are summarized in Table I.
CONCLUSIONS
In conclusion, the present work offers a simple procedure promoted by inex-
pensive and non-toxic glacial acetic acid as an efficient methodology for the syn-
thesis of 2-aryl-1-(arylmethyl)-1H-benzimidazoles via condensation of aromatic
aldehydes with o-phenylenediamine both under microwave irradiation and con-
ventional thermal heating. A mild, manipulatable procedure, eco-friendly and
green aspects avoiding hazardous solvents, shorter reaction times and high yields
of the products are the advantages of this method.
Acknowledgment. We wish to thank the research council of Bu-Ali Sina University, Ha-
madan, Iran, for financial support to carry out this research.
И З В О Д
КОНДЕНЗАЦИЈА о-ФЕНИЛЕНДИАМИНА И АЛДЕХИДА ДО 2-АРИЛ-1-(АРИЛМЕТИЛ)-
-1H-БЕНЗИМИДАЗОЛА У ПРИСУСТВУ СИРЋЕТНЕ КИСЕЛИНЕ
ПОД УСЛОВИМА МИКРОТАЛАСНОГ ЗРАЧЕЊА
DAVOOD AZARIFAR1, MOJGAN PIRHAYATI1, BEHROOZ MALEKI2,
MEHRANGIZ SANGINABADI1 и RAZIEH NEJAT YAMI1
1Faculty of Chemistry, Bu-Ali Sina University, Hamadan-65178 и 2Department of Chemistry,
Sabzevar Tarbiat Moallem University, Sabzevar-397, Iran
Развијен је једноставан, ефикасан и еколошки прихватљив поступак за синтезу раз-
личитих 2-арил-1-(арилметил)-1H-бензимидазола, кондензацијом о-фенилендиамина и ал-
дехида у присуству сирћетне киселине под условима микроталасног озрачивања без инертне
атмосфере и присуства прелазних метала као катализатора.
(Примљено 1. септембра 2009, ревидирано 30. априла 2010)
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