Synthesis of 8-Aryl-7H-acenaphtho[1,2-d]imidazoles Using Fe3O4 NPs&at;GO&at;C4H8SO3H as a Green and Recyclable Magnetic Nanocatalyst

Article abstract of DOI:10.1134/S1070428020060160

Abstract: A general procedure has been developed for the rapid synthesis of 8-aryl-7H-acenaphtho[1,2-d]imidazoles in high yields using Fe₃O₄ NPs&at;GO&at;C₄H₈SO₃H as a green and recyclable magnetic nanocatalyst under reflux conditions. The nanocatalyst was prepared and characterized by FT-IR, XRD, and EDX data. A variety of aromatic aldehydes underwent condensation with NH₄OAc and acenaphthenequinone to give 8-aryl-7H-acenaphtho[1,2-d]imidazole derivatives. The use of magnetic nanoparticles, easy separation of the catalyst with an external magnet, high yields, and short reaction times are the main advantages of this catalytic method.

Full text of DOI:10.1134/S1070428020060160

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 6, pp. 1070–1076. © Pleiades Publishing, Ltd., 2020.
Synthesis of 8-Aryl-7H-acenaphtho[1,2-d]imidazoles
Using Fe3O4 NPs@GO@C4H8SO3H as a Green and Recyclable
Magnetic Nanocatalyst
F. Hasanzadeha and F. K. Behbahania,*
a Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, 314/85313 Iran
*e-mail: farahnazkargar@yahoo.com
Received January 4, 2020; revised March 19, 2020; accepted March 21, 2020
Abstract—A general procedure has been developed for the rapid synthesis of 8-aryl-7H-acenaphtho[1,2-d]-
imidazoles in high yields using Fe3O4 NPs@GO@C4H8SO3H as a green and recyclable magnetic nanocatalyst
under reflux conditions. The nanocatalyst was prepared and characterized by FT-IR, XRD, and EDX data.
A variety of aromatic aldehydes underwent condensation with NH4OAc and acenaphthenequinone to give
8-aryl-7H-acenaphtho[1,2-d]imidazole derivatives. The use of magnetic nanoparticles, easy separation of the
catalyst with an external magnet, high yields, and short reaction times are the main advantages of this catalytic
method.
Keywords: magnetic nanocatalyst, acenaphthoquinone, imidazole, Fe3O4 NPs@GO@C4H8SO3H
DOI: 10.1134/S1070428020060160
INTRODUCTION
tion [20] and between 1,3-oxazolium-5-olates and
N-(arylmethylidene)benzenesulfonamides [21] have
also been reported. Multicomponent reactions (MCRs)
are a very powerful tool in organic and medicinal
chemistry for the preparation of bulky products in
a one-pot fashion from simple starting materials.
A combination of magnetic nanocatalysts and multi-
component reactions could provide efficient and sus-
tainable procedures for green syntheses [22]. More-
over, to the best of our knowledge, Fe3O4 NPs@GO@·
C4H8SO3H as a new reusable heterogeneous nanocata-
lyst has not been utilized previously for one-pot pre-
paration of 8-aryl-7H-acenaphtho[1,2-d]imidazoles.
Therefore, in continuation of our studies on the synthe-
sis of heterocyclic compounds [23–27], we examined
a wide variety of substituted benzaldehydes as starting
materials to establish the catalytic importance of Fe3O4
NPs@GO@C4H8SO3H for one-pot multicomponent
Imidazoles as an important class of heterocyclic
compounds reveal various biological activities such as
herbicidal, antiallergic, analgesic, antidepressant, anti-
tubercular, anticancer, anti-inflammatory, antifungal,
and antiviral [1–9]. Imidazole ring is present in histi-
dine [10] and the related hormone histamine [11], and
some of imidazole derivatives are employed in elec-
tronic and optoelectronic devices [12]. Tetrasubstituted
imidazoles have been synthesized by the four-com-
ponent cyclocondensation of a 1,2-diketone, aldehyde,
primary amine, and ammonium acetate using various
Lewis or protic acids as catalysts, namely BF3–SiO2
[13], silica supported NaHSO4 [14], HPA-EtOH [15],
L-proline [16], K5CoW12O40·3H2O [17], and HY zeo-
lite–Cu(NO3)2 [19]. reactions between a 1,2-diketone,
nitrile, and primary amine under microwave irradia-
Scheme 1.
O
O
O
H
Fe3O4 NPs@GO@C4H8SO3H
EtOH, reflux
N
R
NH4OAc
+
+
N
H
R
1
2
3a–3j
4a–4j
R = 3-NO2 (a), 3-OH (b), 4-Me (c), 4-Br (d), 4-F (e), H (f), 2-OH (g), 2-OH-3-OMe (h), 2-OMe (i), 2,6-Cl2 (j).
1070

SYNTHESIS OF 8-ARYL-7H-ACENAPHTHO[1,2-d]IMIDAZOLES
1071
synthesis of 8-aryl-7H-acenaphtho[1,2-d]imidazoles
via condensation with acenaphthenequinone and am-
monium acetate (Scheme 1).
(~1385 cm–1) (Fig. 1a). The presence of Fe–O band
(~564.13 cm-1) in the FT-IR spectrum of Fe3O4 NPs@·
GO confirms that Fe3O4 NPs are located on the GO
structure (Fig. 1b). Figure 1c shows new bands at 2919
and 1029 cm–1 which were assigned to stretching
vibrations of Csp3–H and C–S bonds, respectively,
indicating that butane-1,4-sultone was loaded on Fe3O4
NPs@GO@C4H8SO3H.
RESULTS AND DISCUSSION
Initially, graphene oxide (GO) was synthesized
from graphite according to procedure described in [29],
and Fe3O4 NPs@GO and Fe3O4 NPs@GO@·
C4H8SO3H were prepared as reported in [30]. The
synthesis of Fe3O4 NPs@GO@C4H8SO3H, the growth
of Fe3O4 nanoparticles, and the loading of C4H8SO3H
onto graphene oxide are illustrated by Scheme 2.
The XRD pattern of the prepared Fe3O4 NPs@·
GO@C4H8SO3H composite is shown in Fig. 2. The
peaks appearing at 30.22, 35.62, 43.62, 53.92, 57.32,
and 62.77° confirmed loading of Fe3O4 NPs on GO.
These peaks are due to the cubic spinel crystal planes
of Fe3O4. The presence of butane-1,4-sultone groups
on the surface of Fe3O4NPs@GO was further con-
firmed by energy dispersive spectroscopy (EDS)
(Fig. 3). According to the EDS data, the prepared cata-
lyst contains 30.14% of carbon, 33.56% of oxygen;
1.74% of sulfur, and 35.69% of iron.
To confirm the structure of the nanocatalyst, its FT-
IR spectrum was measured (Fig. 1). The FT-IR spec-
trum of graphene oxide exhibits absorption bands for
the functionalities containing oxygen atoms such as
OH group (~3435 cm–1), carboxylic C=O group
(~1719 cm–1), and C=C (~1585 cm–1) and C–O bonds
Scheme 2.
FeCl3
O
S
O
O
Fe3O4 NPs@GO
Graphene oxide
Fe3O4 NPs@GO@C4H8SO3H
Graphite
SO3H
HO3S
O
HO
O
Fe3O4
SO3H
HO
Fe3O4
O
O4Fe3
O
O
O
Fe3O4
Fe3O4
O
O4Fe3
Fe3O4
OH
HO
Fe3O4
Fe3O4
O
Fe3O4
O4Fe3
O
O
O
SO3H
SO3H
Fe3O4 NPs@GO@C4H8SO3H
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

HASANZADEH, BEHBAHANI
1072
As noted above, Fe3O4 NPs@GO@C4H8SO3H has
(a)
not been used previously for the synthesis of 8-aryl-
7H-acenaphtho[1,2-d]imidazoles. Therefore, we decid-
ed to use this acidic magnetic nanocatalyst for the
three-component condensation of substituted benzalde-
hydes, acenaphthenequinone, and ammonium acetate.
For this propose, the effects of catalyst amount, tem-
perature, and solvent nature were investigated in the
model reaction with unsubstituted benzaldehyde. The
results showed that the catalyst worked more efficiently
in ethanol under reflux conditions (Table 1). The reac-
tion was then performed in the presence of various
amounts of Fe3O4 NPs@GO@C4H8SO3H to examine
their catalytic activity. An amount of 0.1 g was found
to be most effective to afford the desired product in
98% yield (Table 1).
(b)
(c)
To investigate the substituent effect, a wide variety
of aromatic aldehydes containing electron-withdrawing
or electron-donating groups were utilized. Aromatic
aldehydes with both electron-donating and electron-
withdrawing groups reacted under the selected con-
ditions in short reaction times (Table 2). The yields
were good to excellent without formation of any by-
products such as oxidation products of aldehydes, etc.,
which are normally formed under strongly acidic
conditions. In each case, the reaction profile was clean,
and this one-pot three-component procedure revealed
some advantages over existing methods. The other
features of this new method are simple isolation and
purification of the products, easy separation of the
catalyst by an external magnet and its repeated use.
4000
3000
2000
1500
1000
500
ν, cm–1
Fig. 1. FT-IR spectra of (a) graphene oxide (GO), (b) GO@·
Fe3O4 NPs, and (c) GO@Fe3O4 NPs@C4H8SO3H.
2500
2000
1500
1000
500
0
To show the merits of this procedure in comparison
with the previously reported protocols, we compared
the synthesis of 8-phenyl-7H-acenaphtho[1,2-d]imid-
azole (4f) under different conditions (Table 3). The
advantages of our procedure are the use of Fe3O4
NPs@GO@C4H8SO3H as heterogeneous, reusable,
and magnetically separable catalyst, excellent yield,
short reaction time, and mild reaction condition, which
are very important for chemical industry.
0
20
40
2θ, deg
60
80
Fig. 2. XRD pattern of Fe3O4 NPs@GO @C4H8SO3H.
500
400
300
200
100
O Kα
Fe Lα
A plausible mechanism for the formation of 8-aryl-
7H-acenaphtho[1,2-d]imidazoles from aldehydes, ace-
naphthenequinone, and ammonium acetate is given in
Scheme 3.
Fe Kβ
S Kβ
Si Kα
Al Kα
Mg Kα
EXPERIMENTAL
S Kα
Fe Kα
The melting points were measured in capillary tubes
with an Electrothermal 9200 apparatus. The IR spectra
were recorded on a Perkin Elmer FT-IR spectrometer
0
0
5
10
15
E, keV
1
Fig. 3. EDS pattern of Fe3O4 NPs@GO@C4H8SO3H.
between 4000 and 400 cm–1. The H NMR spectra
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

SYNTHESIS OF 8-ARYL-7H-ACENAPHTHO[1,2-d]IMIDAZOLES
1073
Table 1. The effects of the catalyst amount, temperature, and solvent in the synthesis of 8-phenyl-7H-acenaphto[1,2-d]-
imidazole (4f) in the presence of Fe3O4 NPs@GO@C4H8SO3Ha
Amount of the catalyst, g
Solvent
EtOH
EtOH
EtOH
EtOH
THF
Temperature, °C
Reflux
Reflux
Reflux
70
Reaction time, min
Yield, %
84
0.05
0.08
0.09
0.09
0.1
7
7
87
9
94
5
94
75
8
95
0.1
CHCl3
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
80
10
8
80
0.1
75
90
0.1
Reflux
Reflux
Reflux
Reflux
Reflux
5
98
0.12
0.15
0.17
0.2
8
95
8
85
10
12
84
85
a
Benzaldehyde (1 mmol), acenaphthenequinone (1 mmol), ammonium acetate (2 mmol) and Fe3O4 NPs@GO@C4H8SO3H in a solvent
(10 mL)
Table 2. Synthesis of 8-aryl-7H-acenaphto[1,2-d]imidazoles 4a–4j using Fe3O4 NPs@GO@C4H8SO3H
Compound no.
R
Reaction time, min
Yield, %
82
4a
4b
4c
4d
4e
4f
3-NO2
15
7
3-OH
4-Me
96
5
98
4-Br
8
92
4-F
10
5
94
H
98
4g
4h
4i
2-OH
2-OH-3-OMe
2-OMe
2,6-Cl2
9
94
8
96
12
10
94
4j
95
Table 3. Comparison of different reaction conditions for the synthesis of 4f
Catalyst
Reaction time, min
Yield, %
86
Solvent
Reference
[28]
Nano-SnO2
Nano-SiO2
Nano-ZrO2
Nano-ZnO
150
600
360
240
240
180
5
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
40
[28]
50
[28]
60
[28]
Nano-Fe2O3
65
[28]
NH3/NH4Cl
80
[30]
Fe3O4 NPs@GO@C4H8SO3H
98
This work
were obtained on a Bruker DRX- 300 NMR instrument
operating at 300 MHz. Analytical TLC of all reactions
was performed on precoated silica gel plates (silica
gel 60 F-254 on aluminum, Merck). Elemental analyses
(EDS) and X-ray diffraction (XRD) analysis of the
catalyst were carried out by a PW1840-Philips instru-
ment with Cu Kα radiation.
Synthesis of 8-aryl-7H-acenaphtho[1,2-d]imid-
azoles 4a–4j using Fe3O4 NPs@GO@C4H8SO3H
(general procedure). A mixture of aldehyde 3a–3j
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

HASANZADEH, BEHBAHANI
1074
Scheme 3.
NH4OAc
SO3H
O
H
O
H
NH3
H2N
NH2
SO3H
O
O
N
SO3H
HN
–2H2O
H
N
N
(1 mmol), acenaphthenequinone (1 mmol), ammonium
acetate (2 mmol), and Fe3O4 NPs@GO@C4H8SO3H
(0.1 g) in EtOH (10 mL) was refluxed for a time indicated
in Table 2. The progress of the reaction was monitored
by TLC. After completion of the reaction, the catalyst
was separated by an external magnet, the solvent was
evaporated, and the residue was recrystallized from
aqueous ethanol.
1384 (C–CH3), 1108 (C–N), 775 (δC-H, out-of-plane).
1H NMR spectrum (DMSO-d6): 2.42 s (3H), 7.25 m
(3H), 7.47 d (2H), 7.67 d (3H), 7.85 d (1H).
8-(4-Bromophenyl)-7H-acenaphtho[1,2-d]imid-
azole (4d). Yield 92%, brown solid, mp 262–264°C
[28]. IR spectrum (KBr), ν, cm–1: 3436 (N–H), 3094
(C–Harom), 1656 (C=N), 1607 (δN–H), 1484, 1417
(C=C), 1384 (C–N), 762 (δC–H, out-of-plane), 683
(C–Br). 1H NMR spectrum (DMSO-d6), δ, ppm: 8.88 d
(1H, J = 7.6 Hz), 8.77 d (1H, J = 8 Hz), 8.43 d (1H, J =
6.8 Hz), 8.35 s (1H), 8.31 d (1H, J = 7 Hz), 8.15 d (1H,
J = 7 Hz), 8.08–8.10 m (2H), 7.90–7.83 m (4H), 7.79–
7.81 m (1H), 7.64–7.70 m (2H).
8-(3-Nitrophenyl)-7H-acenaphtho[1,2-d]imid-
azole (4a). Yield 82%, orange solid, mp 227–230°C
[30]. IR spectrum (KBr), ν, cm–1: 3433 (N–H), 3049
(C–Harom), 1683 (C=N), 1525 (C=C), 1500 (NO2),
1345 (C–N), 766 (δC–H, out-of-plane). 1H NMR spec-
trum (DMSO-d6), δ, ppm: 7.63–7.5 m (7H, Harom),
8.2 d (1H), 8.4 d (1H), 8.8 s (1H).
8-(4-Fluorophenyl)-7H-acenaphtho[1,2-d]imid-
azole (4e). Yield 94%, light brown solid, mp 301–
303°C [28]. IR spectrum (KBr), ν, cm–1: 3480 (N–H),
3130 (C–Harom), 1674 (C=N), 1607 (δN–H), 1511,
1417 (C=C), 1384 (C–N), 1236 (C–F), 762 (δC–H,
3-(7H-Acenaphtho[1,2-d]imidazol-8-yl)phenol
(4b). Yield 96%, brown solid, mp 330–332°C [28].
IR spectrum (KBr), ν, cm–1: 3392 (N–H, O–H), 3055
(C–Harom), 1678 (C=N), 1590 (δ N–H), 1480 (C=C),
1277 (C–N), 1227 (C–O), 770 (δC–H, out-of-plane).
1H NMR spectrum (CDCl3), δ, ppm: 8.88 d.d (1H,
J = 7.6, 1.2 Hz), 8.77 d.d (1H, J = 7.6, 1.2 Hz), 8.43 d
(1H, J = 6.8 Hz), 8.33 d.d (1H, J = 8, 0.8 Hz), 8.04–
8.10 m (2H), 7.83–7.89 m (3H), 7.79 s (1H), 7.63–
7.70 m (2H).
1
out-of-plane). H NMR spectrum (DMSO-d6), δ, ppm:
8.88 d.d (1H, J = 7.2, 1.2 Hz), 8.77 d.d (1H, J = 7.2,
1.2 Hz), 8.43 d (1H, J = 6.4 Hz), 8.33 d.d (1H, J = 8,
1.2 Hz), 8.08–8.10 m (2H), 7.81–7.89 m (2H), 7.79 s
(1H), 7.63–7.70 m (2H).
8-Phenyl-7H-acenaphtho[1,2-d]imidazole (4f).
Yield 91%, yellow solid, mp 270–272°C [30]. IR spec-
trum (KBr), cm–1: 3434 (N–H), 1664 (C=N), 1603
(δN–H), 1590 (C=C), 1227 (C–N), 776 (δC–H, out-of-
plane). 1H NMR spectrum (DMSO-d6), δ, ppm: 12.91 s
(1H), 7.26 m (2H), 7.46 m (1H), 7.53 m (2H), 7.62 m
(2H), 8.18 m (2H).
8-(4-Methylphenyl)-7H-acenaphtho[1,2-d]imid-
azole (4c). Yield 98%, orange solid, mp. 230–232°C
[30]. IR spectrum (KBr), ν, cm–1: 3436 (N–H), 3041
(C–Harom), 1687 (C=N), 1608 (δN–H), 1595 (C=C),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

SYNTHESIS OF 8-ARYL-7H-ACENAPHTHO[1,2-d]IMIDAZOLES
1075
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2-(7H-Acenaphtho[1,2-d]imidazol-8-yl)phenol
(4g). Yield 94%, brown solid, mp 294–297°C [28].
IR spectrum (KBr), cm–1: 3435 (N–H, O–H), 3055
(C–Harom), 1697 (C=N), 1657 (C=C), 1591 (δN–H),
1384 (C–N), 1287 (C–O), 760 (δC–H, out-of-plane).
1H NMR spectrum (DMSO-d6), δ, ppm: 6.86–6.93 d
(2H, J = 7.5 Hz), 6.97–7.01 d (2H, J = 7.8 Hz), 7.2–
7.52 m (10H), 12.49 br.s (NH).
2-(7H-Acenaphtho[1,2-d]imidazol-8-yl)-6-me-
thoxyphenol (4h). Yield 96%, brown solid, mp 102–
105°C. IR spectrum (KBr), ν, cm–1: 3436 (N–H, OH),
3098 (C–Harom), 1653 (C=N), 1583 (N–H), 1619
(C=C), 1584 (C–N), 1253 (C–O), 719 (δC–H, out-of-
1
plane). H NMR spectrum (DMSO-d6), δ, ppm: 6.99–
7.04 d (2H, J = 8 Hz), 7.51–7.86 m (10H), 7.87–7.90 d
(2H, J = 8.5 Hz), 12.61 br.s (NH). Mass spectrum:
m/z 314.10 (Irel 21%) [M + 1]+. Found, %: C 76.40;
H 4.46; N 8.88. C20H14N2O2. Calculated, %: C 76.42;
H 4.49; N 8.91.
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8-(2-Methoxyphenyl)-7H-acenaphtho[1,2-d]-
imidazole (4i). Yield 94%, orange solid, mp 220–
225°C. IR spectrum (KBr), ν, cm–1: 3435 (N–H), 1603
(C=N), 1583 (δN–H), 1478 (C=C), 1384 (C–N) 1243
(C–O), 767 (δC–H, out-of-plane). H NMR spectrum
(DMSO-d6), δ, ppm: 3.07 s (3H, OMe), 7.80–7.82 m
(5H, Harom), 8.05 d (4H, Harom, J = 7.0 Hz), 8.26 d (4H,
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Tetrahedron Lett., 2008, vol. 49, p. 2575.
H
arom, J = 8.3 Hz), 8.40 d (1H, Harom, J = 8.0 Hz). Mass
spectrum: m/z 298.11 (Irel 20%) [M + 1]+. Found, %:
C 80.50; H 4.71; N 9.36. C20H14N2O. Calculated, %:
C 80.52; H 4.73; N 9.39.
https://doi.org/10.1016/j.tetlet.2008.02.100
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8-(2,6-Dichlorophenyl)-7H-acenaphtho[1,2-d]-
imidazole (4j). Yield 95%, yellow solid, mp 250–
258°C. IR spectrum (KBr), cm–1: 3413 (N–H), 3055
(C–Harom), 1678 (C=N), 1591 (δN–H), 1480 (C=C),
1227 (C–N) 819 (δC–H, out-of-plane), 770 (C–Cl).
1H NMR spectrum (DMSO-d6): 7.82–7.90 m (4H,
H
arom), 8.12 d (3H, Harom, J = 7.0 Hz), 7.29–8.36 m
(4H, Harom), 8.36 d (1H, Harom, J = 7.3 Hz). Mass spec-
trum: m/z 336.02 (Irel 20%) [M + 1]+. Found, %:
C 67.60; H 2.95; Cl 21.00; N 8.29. C19H10Cl2N2.
Calculated, %: C 67.68; H 2.99; Cl 21.03; N 8.31.
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CONFLICT OF INTEREST
The authors declare the absence of conflict of interest.
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